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626-67-5

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626-67-5 Usage

Description

This simple piperidine derivative has been obtained from Girgensohnia diptera Bge. It is optically inactive and furnishes a crystalline picrate, m.p. 15 I-2°C and a picrolonate, m.p. 226°C.

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Different sources of media describe the Uses of 626-67-5 differently. You can refer to the following data:
1. Reactant for: ·sp3 C-H Bond activation with ruthenium(II) catalysts and C(3)-alkylation of cyclic amines ·One-pot synthesis of Z-cinnamic acids Reactant for synthesis of: ·Unsymmetrical ureas ·Antibacterial imidazolium, pyrrolidinium, and piperidinium salts ·C1-C16 segment of goniodomin A via palladium-catalyzed organostannane thioester coupling ·Multi-targeted inhibitors of insulin-like growth factor-1 receptor and members of ErbB-family receptor kinases
2. 1-Methylpiperidine is a reactant for sp3 C-H Bond activation with ruthenium(II) catalysts and C(3)-alkylation of cyclic amines, One-pot synthesis of Z-cinnamic acids. It is used in the synthesis of Unsymmetrical ureas, Antibacterial imidazolium, pyrrolidinium, and piperidinium salts, C1-C16 segment of goniodomin A via palladium-catalyzed organostannane thioester coupling.
3. Reactant for: sp3 C-H Bond activation with ruthenium(II) catalysts and C(3)-alkylation of cyclic aminesOne-pot synthesis of Z-cinnamic acidsReactant for synthesis of:Unsymmetrical ureasAntibacterial imidazolium, pyrrolidinium, and piperidinium saltsC1-C16 segment of goniodomin A via palladium-catalyzed organostannane thioester couplingMulti-targeted inhibitors of insulin-like growth factor-1 receptor and members of ErbB-family receptor kinases

General Description

A colorless liquid with the odor of pepper. Density 0.816 g / cm3 and flash point 38°F. May irritate skin and eyes. Vapors heavier than air. Used as a solvent and to make other chemicals.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

N-Methylpiperidine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Highlyflammable

Safety Profile

Poison by intraperitoneal and subcutaneous routes. A very dangerous fire hazard when exposed to heat or flame. When heated to decomposition it emits toxic fumes of NOx.

References

Jurashevskii, Stepanov,J. Gen. Chem. USSR, 9,2203 (1939)

Check Digit Verification of cas no

The CAS Registry Mumber 626-67-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 6 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 626-67:
(5*6)+(4*2)+(3*6)+(2*6)+(1*7)=75
75 % 10 = 5
So 626-67-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H13N/c1-7-5-3-2-4-6-7/h2-6H2,1H3/p+1

626-67-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L03398)  1-Methylpiperidine, 99%   

  • 626-67-5

  • 10g

  • 180.0CNY

  • Detail
  • Alfa Aesar

  • (L03398)  1-Methylpiperidine, 99%   

  • 626-67-5

  • 100g

  • 222.0CNY

  • Detail
  • Alfa Aesar

  • (L03398)  1-Methylpiperidine, 99%   

  • 626-67-5

  • 500g

  • 935.0CNY

  • Detail
  • Aldrich

  • (M72609)  N-Methylpiperidine  99%

  • 626-67-5

  • M72609-100ML

  • 402.48CNY

  • Detail
  • Aldrich

  • (M72609)  N-Methylpiperidine  99%

  • 626-67-5

  • M72609-500ML

  • 1,477.71CNY

  • Detail

626-67-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Methylpiperidine

1.2 Other means of identification

Product number -
Other names 1-methylpiperidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:626-67-5 SDS

626-67-5Synthetic route

piperidine
110-89-4

piperidine

methanol
67-56-1

methanol

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With P(C4H9)3; ruthenium trichloride at 220℃; for 5h; Product distribution; Mechanism; also with or without other catalyst, other phosphines, other temperatures,;100%
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 100℃; for 3h;100%
Pt on TiO2 for 20h; Ambient temperature; Irradiation;93.4%
N-methyl-3,4-didehydropiperidine
694-55-3

N-methyl-3,4-didehydropiperidine

carbon monoxide
201230-82-2

carbon monoxide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With hydrogen; di-μ-chlorobis(norbornadiene)dirhodium(I) In benzene at 100℃; under 60004.8 Torr; for 6h;100%
N-Formylpiperidine
2591-86-8

N-Formylpiperidine

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With 1,1,3,3-Tetramethyldisiloxane; [((CH3)5C5)IrCl((CH3)2NC6H3C5H4N)]; trityl tetrakis(pentafluorophenyl)borate In 1,1,2,2-tetrachloroethane at 100℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction;99%
With phenylsilane; caesium carbonate at 25℃; for 30h; Schlenk technique;51%
With lithium aluminium tetrahydride; diethyl ether
piperidine
110-89-4

piperidine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With 3 % platinum on carbon; hydrogen; toluene-4-sulfonic acid at 120℃; under 30003 Torr; for 3h; Reagent/catalyst; Inert atmosphere; Autoclave;99%
piperidine
110-89-4

piperidine

formaldehyd
50-00-0

formaldehyd

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With acetic acid at 30℃; for 2h;98%
With diiodo(p-cymene)ruthenium(II) dimer In water at 60℃; for 2h;95%
Stage #1: piperidine; formaldehyd With hydrogenchloride In methanol at 20℃;
Stage #2: With N-methylpiperidine zinc borohydride In methanol at 20℃; for 0.1h;
89%
piperidine
110-89-4

piperidine

(1H-indol-3-yl)dimethylsulfonium perchlorate

(1H-indol-3-yl)dimethylsulfonium perchlorate

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

3-methylthioindole
40015-10-9

3-methylthioindole

Conditions
ConditionsYield
at 106℃; for 1h;A n/a
B 96%
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With methylamine95%
1,1'-Dimethyl-3-(2'-piperidyl)-1,4,5,6-tetrahydropyridin
54105-23-6

1,1'-Dimethyl-3-(2'-piperidyl)-1,4,5,6-tetrahydropyridin

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

1-methylpiperidin-2-one
931-20-4

1-methylpiperidin-2-one

C

1-Methyl-3-(5-methylamino-pentyliden)piperidin
106940-68-5

1-Methyl-3-(5-methylamino-pentyliden)piperidin

Conditions
ConditionsYield
With hydrogenchloride; sodium tetrahydroborate In ethanol for 18h;A n/a
B n/a
C 88%
n-decyl magnesium bromide
17049-50-2

n-decyl magnesium bromide

benzophenone N-methyl-N,N-pentane-1,5-diylhydrazonium iodide
13134-23-1

benzophenone N-methyl-N,N-pentane-1,5-diylhydrazonium iodide

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

Benzophenone imine
1013-88-3

Benzophenone imine

C

decane
124-18-5

decane

D

icosane
112-95-8

icosane

E

1-Decene
872-05-9

1-Decene

Conditions
ConditionsYield
In diethyl ether Product distribution; Mechanism; Heating; other quaternary hydrazonium salts, other alkylmagnesium halides;A 85%
B 84%
C 51%
D 21%
E 25%
methanol
67-56-1

methanol

C8H16LiN
173978-45-5

C8H16LiN

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
Ambient temperature;82%
N-methylpiperidine-N-oxide
17206-00-7

N-methylpiperidine-N-oxide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With titanium tetrachloride; sodium iodide In acetonitrile at 20℃; for 0.0833333h;81%
Erhitzen;
pyridine
110-86-1

pyridine

carbon dioxide
124-38-9

carbon dioxide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With 5 wt% Pd/C; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 160℃; under 75007.5 Torr; for 6h; Autoclave;81%
piperidine
110-89-4

piperidine

carbon dioxide
124-38-9

carbon dioxide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With 5 wt% Pd/C; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 160℃; under 75007.5 Torr; for 6h; Autoclave;77%
With diphenylsilane; cesium formate In acetonitrile at 50℃; under 750.075 Torr; for 6h; Green chemistry;64%
With iron(II) tetrafluoroborate hexahydrate; phenylsilane; tris(2-diphenylphosphinoethyl)phosphine In tetrahydrofuran at 100℃; under 750.075 - 2250.23 Torr; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Glovebox; Sealed tube;15%
piperidine-1-carboxylic acid methyl ester
1796-27-6

piperidine-1-carboxylic acid methyl ester

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Heating;76%
piperidine
110-89-4

piperidine

O-methyl adamantane-1-carbothioate
123933-30-2

O-methyl adamantane-1-carbothioate

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

S-methyl 1-adamantanecarbothioate

S-methyl 1-adamantanecarbothioate

C

S-piperidinium 1-adamantanecarbothioate

S-piperidinium 1-adamantanecarbothioate

Conditions
ConditionsYield
for 0.5h; Heating;A n/a
B 12%
C 69%
O-methyl adamantane-1-carbothioate
123933-30-2

O-methyl adamantane-1-carbothioate

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

S-methyl 1-adamantanecarbothioate

S-methyl 1-adamantanecarbothioate

C

S-piperidinium 1-adamantanecarbothioate

S-piperidinium 1-adamantanecarbothioate

Conditions
ConditionsYield
With piperidine for 0.5h; Heating;A n/a
B 12%
C 69%
N-Cyan-N-(2,6-dimethylphenyl)-α-alaninmethylester
136672-60-1

N-Cyan-N-(2,6-dimethylphenyl)-α-alaninmethylester

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

N-(2,6-Dimethylphenyl)-5-methyl-imidazolidin-2,4-dion
136672-58-7

N-(2,6-Dimethylphenyl)-5-methyl-imidazolidin-2,4-dion

Conditions
ConditionsYield
With piperidine at 100℃; for 3h;A n/a
B 64%
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

tributyl(pentamethylenecarbamoyloxy)stannane

tributyl(pentamethylenecarbamoyloxy)stannane

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

tri-n-butyl-tin hydride
688-73-3

tri-n-butyl-tin hydride

Conditions
ConditionsYield
In diethyl ether boiling (stirring, 4 h); water addn., separation of org. phase, drying over CaCl2, solvent evapn., distn. (vacuum);A n/a
B 60%
N-methyl-3,4-didehydropiperidine
694-55-3

N-methyl-3,4-didehydropiperidine

carbon monoxide
201230-82-2

carbon monoxide

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

N-methyl-piperidine-4-carboxaldehyde
50675-21-3

N-methyl-piperidine-4-carboxaldehyde

C

1-methylpiperidine-3-carboxaldehyde
99658-56-7

1-methylpiperidine-3-carboxaldehyde

Conditions
ConditionsYield
With hydrogen; carbonylhydridetris(triphenylphosphine)rhodium(I) In benzene at 100℃; under 60004.8 Torr; for 6h;A 2%
B 59%
C 39%
With hydrogen; di-μ-chlorobis(norbornadiene)dirhodium(I); triphenylphosphine In benzene at 100℃; under 60004.8 Torr; for 6h; Product distribution; various catalysts, formed in situ from various phosphines;A 3%
B 56%
C 41%
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

triethyltin N,N-pentamethylenecarbamate
116019-84-2

triethyltin N,N-pentamethylenecarbamate

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

triethylstannane
997-50-2

triethylstannane

Conditions
ConditionsYield
In diethyl ether boiling (stirring, 3 h); water addn., separation of org. phase, drying over CaCl2, solvent evapn., distn. (vacuum);A n/a
B 56%
piperidine
110-89-4

piperidine

trimethylbismuthine
593-91-9

trimethylbismuthine

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With copper diacetate In dichloromethane for 24h; Ambient temperature;49%
1-isopropyl-1-methyl-piperidinium; iodide
84437-36-5

1-isopropyl-1-methyl-piperidinium; iodide

A

N-isopropylpiperidine
766-79-0

N-isopropylpiperidine

B

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With sodium thiophenolate In acetonitrile; butanone Heating;A 45%
B 30%
piperidine
110-89-4

piperidine

methyldiphenylbismuthine
74724-75-7

methyldiphenylbismuthine

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With copper diacetate In dichloromethane for 24h; Ambient temperature;31%
piperidine
110-89-4

piperidine

methyl iodide
74-88-4

methyl iodide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

piperidine
110-89-4

piperidine

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With diethyl ether; phenyllithium anschliessend mit Methyljodid;
Multi-step reaction with 2 steps
1: 1-butyl-3-methylimidazolium chloride; hydrogen; 5 wt% Pd/C / 6 h / 160 °C / 75007.5 Torr / Autoclave
2: hydrogen; 5 wt% Pd/C; potassium tert-butylate; 1-butyl-3-methylimidazolium Tetrafluoroborate / 8 h / 160 °C / 45004.5 Torr / Autoclave
View Scheme
Multi-step reaction with 2 steps
1: 1-hexyl-3-methylimidazolium tetrafluoroborate; hydrogen; 5 wt% Pd/C / 6 h / 160 °C / 75007.5 Torr / Autoclave
2: hydrogen; 5 wt% Pd/C; potassium tert-butylate; 1-butyl-3-methylimidazolium Tetrafluoroborate / 8 h / 160 °C / 45004.5 Torr / Autoclave
View Scheme
pyridine
110-86-1

pyridine

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With methanol; kieselguhr; nickel at 220℃; under 58840.6 Torr; Hydrogenation;
Multi-step reaction with 2 steps
1: ethanol / 6 h / 80 °C / 3750.38 Torr
2: hydrogen / 12 h / 130 °C / 45004.5 Torr
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; 5 wt% Pd/C; 1-butyl-3-methylimidazolium Tetrafluoroborate / 6 h / 120 °C / 37503.8 Torr / Autoclave
2: piperidine; hydrogen; 5 wt% Pd/C; 1-butyl-3-methylimidazolium Tetrafluoroborate / 12 h / 160 °C / 45004.5 Torr
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; 5 wt% Pd/C; 1-butyl-3-methylimidazolium Tetrafluoroborate / 6 h / 120 °C / 37503.8 Torr / Autoclave
2: N-methylcyclohexylamine; hydrogen; 5 wt% Pd/C; 1-butyl-3-methylimidazolium Tetrafluoroborate / 8 h / 160 °C / 45004.5 Torr / Autoclave
3: hydrogen; 5 wt% Pd/C; potassium tert-butylate; 1-butyl-3-methylimidazolium Tetrafluoroborate / 8 h / 160 °C / 45004.5 Torr / Autoclave
View Scheme
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
at 60℃; elektrochemische Reduktion an einer Cadmium-Kathode;
N-methyladipinimide
25077-25-2

N-methyladipinimide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With tetrahydrofuran; sodium aluminum tetrahydride
With lithium aluminium tetrahydride; diethyl ether
N-Ethoxycarbonylpiperidine
5325-94-0

N-Ethoxycarbonylpiperidine

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

2-iodo-propane
75-30-9

2-iodo-propane

1-isopropyl-1-methyl-piperidinium; iodide
84437-36-5

1-isopropyl-1-methyl-piperidinium; iodide

Conditions
ConditionsYield
In chloroform at 60℃; for 8h;100%
In chloroform Heating;
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

1-iodo-butane
542-69-8

1-iodo-butane

1-butyl-1-methylpiperidinium iodide
37971-78-1

1-butyl-1-methylpiperidinium iodide

Conditions
ConditionsYield
In chloroform at 60℃; for 6h;100%
In chloroform Heating;
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

[13C]methyl iodide
4227-95-6

[13C]methyl iodide

N,N-13CH3,CH3-piperidinium iodide

N,N-13CH3,CH3-piperidinium iodide

Conditions
ConditionsYield
100%
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

propyl bromide
106-94-5

propyl bromide

1-propyl-1-methyl-piperidinium bromide
88840-42-0

1-propyl-1-methyl-piperidinium bromide

Conditions
ConditionsYield
In chloroform at 60℃; for 6h;100%
In ethyl acetate at 20℃; for 12h; Solvent;98%
In chloroform Heating;
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

methyl (2Z)-3-iodoprop-2-enoate
6214-23-9

methyl (2Z)-3-iodoprop-2-enoate

1-((E)-2-Methoxycarbonyl-vinyl)-1-methyl-piperidinium; iodide

1-((E)-2-Methoxycarbonyl-vinyl)-1-methyl-piperidinium; iodide

Conditions
ConditionsYield
In toluene Heating;100%
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

triethylene glycol di-(p-toluenesulfonate)
19249-03-7

triethylene glycol di-(p-toluenesulfonate)

1,8-bis[1-methylpiperidinium]-3,6-dioxaoctane di(p-toluenesulfonate)

1,8-bis[1-methylpiperidinium]-3,6-dioxaoctane di(p-toluenesulfonate)

Conditions
ConditionsYield
In acetonitrile for 72h; Reflux;100%
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate
62921-74-8

2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate

1-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1-methylpiperidinium p-toluenesulfonate
1492041-52-7

1-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1-methylpiperidinium p-toluenesulfonate

Conditions
ConditionsYield
In acetonitrile at 90℃; for 24h;100%
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

copper(l) cyanide

copper(l) cyanide

[(copper(I)cyanide)(N-methylpiperidine)]
1239956-19-4

[(copper(I)cyanide)(N-methylpiperidine)]

Conditions
ConditionsYield
In further solvent(s) suspn. of Cu complex in NMePipd heated in sealed tube under Ar to 70°C overnight, cooled; ppt. filtered off, washed with Et2O, air dried for 15 min; elem. anal.;99.3%
In neat (no solvent) CuCN suspended in N-Me-piperidine in sealed tube under Ar; mixt. heated to 70°C in oil bath overnight without stirring; cooled; alternatively - vapor diffusion reaction; collected by filtration; washed with Et2O; air dried for 15 min;
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

(x)C4H10O*AlCl3

(x)C4H10O*AlCl3

AlCl3(N-methylpiperidine)
1446025-52-0

AlCl3(N-methylpiperidine)

Conditions
ConditionsYield
In diethyl ether for 4h; Inert atmosphere; Cooling with ice;99%
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

(x)C4H10O*AlI3

(x)C4H10O*AlI3

AlI3(N-methylpiperidine)
1446025-54-2

AlI3(N-methylpiperidine)

Conditions
ConditionsYield
In diethyl ether for 4h; Inert atmosphere; Cooling with ice;99%
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

C6H13N*F6P(1-)*H(1+)

C6H13N*F6P(1-)*H(1+)

Conditions
ConditionsYield
With ammonium hexafluorophosphate In ethanol for 1h; Reflux;99%
N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

4-Phenyl-1-butene
768-56-9

4-Phenyl-1-butene

N-(2-methyl-4-phenylbutyl)piperidine

N-(2-methyl-4-phenylbutyl)piperidine

Conditions
ConditionsYield
With tetrabenzyl titanium; trityl tetrakis(pentafluorophenyl)borate In toluene at 28℃; for 96h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;99%
piperidine
110-89-4

piperidine

methanol
67-56-1

methanol

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With P(C4H9)3; ruthenium trichloride at 220℃; for 5h; Product distribution; Mechanism; also with or without other catalyst, other phosphines, other temperatures,;100%
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 100℃; for 3h;100%
Pt on TiO2 for 20h; Ambient temperature; Irradiation;93.4%
N-methyl-3,4-didehydropiperidine
694-55-3

N-methyl-3,4-didehydropiperidine

carbon monoxide
201230-82-2

carbon monoxide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With hydrogen; di-μ-chlorobis(norbornadiene)dirhodium(I) In benzene at 100℃; under 60004.8 Torr; for 6h;100%
N-Formylpiperidine
2591-86-8

N-Formylpiperidine

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With 1,1,3,3-Tetramethyldisiloxane; [((CH3)5C5)IrCl((CH3)2NC6H3C5H4N)]; trityl tetrakis(pentafluorophenyl)borate In 1,1,2,2-tetrachloroethane at 100℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction;99%
With phenylsilane; caesium carbonate at 25℃; for 30h; Schlenk technique;51%
With lithium aluminium tetrahydride; diethyl ether
piperidine
110-89-4

piperidine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With 3 % platinum on carbon; hydrogen; toluene-4-sulfonic acid at 120℃; under 30003 Torr; for 3h; Reagent/catalyst; Inert atmosphere; Autoclave;99%
piperidine
110-89-4

piperidine

formaldehyd
50-00-0

formaldehyd

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With acetic acid at 30℃; for 2h;98%
With diiodo(p-cymene)ruthenium(II) dimer In water at 60℃; for 2h;95%
Stage #1: piperidine; formaldehyd With hydrogenchloride In methanol at 20℃;
Stage #2: With N-methylpiperidine zinc borohydride In methanol at 20℃; for 0.1h;
89%
piperidine
110-89-4

piperidine

(1H-indol-3-yl)dimethylsulfonium perchlorate

(1H-indol-3-yl)dimethylsulfonium perchlorate

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

3-methylthioindole
40015-10-9

3-methylthioindole

Conditions
ConditionsYield
at 106℃; for 1h;A n/a
B 96%
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With methylamine95%
1,1'-Dimethyl-3-(2'-piperidyl)-1,4,5,6-tetrahydropyridin
54105-23-6

1,1'-Dimethyl-3-(2'-piperidyl)-1,4,5,6-tetrahydropyridin

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

1-methylpiperidin-2-one
931-20-4

1-methylpiperidin-2-one

C

1-Methyl-3-(5-methylamino-pentyliden)piperidin
106940-68-5

1-Methyl-3-(5-methylamino-pentyliden)piperidin

Conditions
ConditionsYield
With hydrogenchloride; sodium tetrahydroborate In ethanol for 18h;A n/a
B n/a
C 88%
n-decyl magnesium bromide
17049-50-2

n-decyl magnesium bromide

benzophenone N-methyl-N,N-pentane-1,5-diylhydrazonium iodide
13134-23-1

benzophenone N-methyl-N,N-pentane-1,5-diylhydrazonium iodide

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

Benzophenone imine
1013-88-3

Benzophenone imine

C

decane
124-18-5

decane

D

icosane
112-95-8

icosane

E

1-Decene
872-05-9

1-Decene

Conditions
ConditionsYield
In diethyl ether Product distribution; Mechanism; Heating; other quaternary hydrazonium salts, other alkylmagnesium halides;A 85%
B 84%
C 51%
D 21%
E 25%
methanol
67-56-1

methanol

C8H16LiN
173978-45-5

C8H16LiN

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
Ambient temperature;82%
N-methylpiperidine-N-oxide
17206-00-7

N-methylpiperidine-N-oxide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With titanium tetrachloride; sodium iodide In acetonitrile at 20℃; for 0.0833333h;81%
Erhitzen;
pyridine
110-86-1

pyridine

carbon dioxide
124-38-9

carbon dioxide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With 5 wt% Pd/C; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 160℃; under 75007.5 Torr; for 6h; Autoclave;81%
piperidine
110-89-4

piperidine

carbon dioxide
124-38-9

carbon dioxide

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With 5 wt% Pd/C; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 160℃; under 75007.5 Torr; for 6h; Autoclave;77%
With diphenylsilane; cesium formate In acetonitrile at 50℃; under 750.075 Torr; for 6h; Green chemistry;64%
With iron(II) tetrafluoroborate hexahydrate; phenylsilane; tris(2-diphenylphosphinoethyl)phosphine In tetrahydrofuran at 100℃; under 750.075 - 2250.23 Torr; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Glovebox; Sealed tube;15%
piperidine-1-carboxylic acid methyl ester
1796-27-6

piperidine-1-carboxylic acid methyl ester

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Heating;76%
piperidine
110-89-4

piperidine

O-methyl adamantane-1-carbothioate
123933-30-2

O-methyl adamantane-1-carbothioate

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

S-methyl 1-adamantanecarbothioate

S-methyl 1-adamantanecarbothioate

C

S-piperidinium 1-adamantanecarbothioate

S-piperidinium 1-adamantanecarbothioate

Conditions
ConditionsYield
for 0.5h; Heating;A n/a
B 12%
C 69%
O-methyl adamantane-1-carbothioate
123933-30-2

O-methyl adamantane-1-carbothioate

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

S-methyl 1-adamantanecarbothioate

S-methyl 1-adamantanecarbothioate

C

S-piperidinium 1-adamantanecarbothioate

S-piperidinium 1-adamantanecarbothioate

Conditions
ConditionsYield
With piperidine for 0.5h; Heating;A n/a
B 12%
C 69%
N-Cyan-N-(2,6-dimethylphenyl)-α-alaninmethylester
136672-60-1

N-Cyan-N-(2,6-dimethylphenyl)-α-alaninmethylester

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

N-(2,6-Dimethylphenyl)-5-methyl-imidazolidin-2,4-dion
136672-58-7

N-(2,6-Dimethylphenyl)-5-methyl-imidazolidin-2,4-dion

Conditions
ConditionsYield
With piperidine at 100℃; for 3h;A n/a
B 64%
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

tributyl(pentamethylenecarbamoyloxy)stannane

tributyl(pentamethylenecarbamoyloxy)stannane

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

tri-n-butyl-tin hydride
688-73-3

tri-n-butyl-tin hydride

Conditions
ConditionsYield
In diethyl ether boiling (stirring, 4 h); water addn., separation of org. phase, drying over CaCl2, solvent evapn., distn. (vacuum);A n/a
B 60%
N-methyl-3,4-didehydropiperidine
694-55-3

N-methyl-3,4-didehydropiperidine

carbon monoxide
201230-82-2

carbon monoxide

A

N-methylcyclohexylamine
626-67-5

N-methylcyclohexylamine

B

N-methyl-piperidine-4-carboxaldehyde
50675-21-3

N-methyl-piperidine-4-carboxaldehyde

C

1-methylpiperidine-3-carboxaldehyde
99658-56-7

1-methylpiperidine-3-carboxaldehyde

Conditions
ConditionsYield
With hydrogen; carbonylhydridetris(triphenylphosphine)rhodium(I) In benzene at 100℃; under 60004.8 Torr; for 6h;A 2%
B 59%
C 39%
With hydrogen; di-μ-chlorobis(norbornadiene)dirhodium(I); triphenylphosphine In benzene at 100℃; under 60004.8 Torr; for 6h; Product distribution; various catalysts, formed in situ from various phosphines;A 3%
B 56%
C 41%

626-67-5Relevant articles and documents

Synthesis and characterization of substituted (aminomethyl)lithium compounds: The structures of [Li2(CH2NPh2)2(THF)3] and [Li4(CH2NC5H10)4(THF)2]

Becke, Frank,Heinemann, Frank W.,Rueffer, Tobias,Wiegeleben, Peter,Boese, Roland,Blaeser, Dieter,Steinborn, Dirk

, p. 205 - 210 (1997)

(Aminomethyl)lithium compounds LiCH2NRR′ · x THF (NRR′ = NMe2 (1a, x = 0), NPhMe (1b, x = 2), NPh2 (1c, x = 1 ... 1,5), NC5H10 (1d, x = 0, NC5H10 = piperidino), and NC7H14 (1e, NC7H14 = 2,6-dimethylpiperidino)) were prepared by the reaction of Bu3SnCH2NRR′ with BuLi. 1a-d were isolated in solid state and characterized by NMR spectroscopy (1H, 13C, 7Li). 1e was obtained in solution and characterized via reaction with MeOH and with benzophenone to generate MeNC7H14 and Ph2C(OH)CH2NC7H14, respectively. Recrystallization of 1c and 1d from n-hexane/THF gives [Li2(CH2NPh2)2(THF)3] (1c′) and [Li4(CH2NC5H10)4(THF)2] (1d′), respectively, whose structures (X-ray) were determined. The dimeric compound 1c′ forms a central planar four-membered Li2C2 ring. One lithium atom is four-coordinated to two methylene carbon atoms (d(Li-C) = 2.246(9), 2.235(9) A) and two oxygen atoms of THF. Unusually, the second lithium exhibits a nearly planar coordination sphere represented by two methylene carbon atoms (d(Li-C) = 2.17(1) and 2.16(1) A) and by the oxygen atom of the disordered THF molecule. 1d′ is a tetrameric species exhibiting a molecular C2 symmetry. The lithium atoms are arranged in a distorted tetrahedron with methylene carbon atoms occupying each face of the tetrahedron.

Reduction of Amides to Amines with Pinacolborane Catalyzed by Heterogeneous Lanthanum Catalyst La(CH2C6H4NMe2- o)3@SBA-15

Guo, Chenjun,Zhang, Fangcao,Yu, Chong,Luo, Yunjie

supporting information, p. 13122 - 13135 (2021/08/31)

Hydroboration of amides is a useful synthetic strategy to access the corresponding amines. In this contribution, it was found that the supported lanthanum benzyl material La(CH2C6H4NMe2-o)3@SBA-15 was highly active for the hydroboration of primary, secondary, and tertiary amides to amines with pinacolborane. These reactions selectively produced target amines and showed good tolerance for functional groups such as -NO2, -halogen, and -CN, as well as heteroatoms such as S and O. This reduction procedure exhibited the recyclable and reusable property of heterogeneous catalysts and was applicable to gram-scale synthesis. The reaction mechanisms were proposed based on some control experiments and the previous literature. This is the first example of hydroborative reduction of amides to amines mediated by heterogeneous catalysts.

Electrochemical Reductive N-Methylation with CO2Enabled by a Molecular Catalyst

Rooney, Conor L.,Wu, Yueshen,Tao, Zixu,Wang, Hailiang

supporting information, p. 19983 - 19991 (2021/12/01)

The development of benign methylation reactions utilizing CO2 as a one-carbon building block would enable a more sustainable chemical industry. Electrochemical CO2 reduction has been extensively studied, but its application for reductive methylation reactions remains out of the scope of current electrocatalysis. Here, we report the first electrochemical reductive N-methylation reaction with CO2 and demonstrate its compatibility with amines, hydroxylamines, and hydrazine. Catalyzed by cobalt phthalocyanine molecules supported on carbon nanotubes, the N-methylation reaction proceeds in aqueous media via the chemical condensation of an electrophilic carbon intermediate, proposed to be adsorbed or near-electrode formaldehyde formed from the four-electron reduction of CO2, with nucleophilic nitrogenous reactants and subsequent reduction. By comparing various amines, we discover that the nucleophilicity of the amine reactant is a descriptor for the C-N coupling efficacy. We extend the scope of the reaction to be compatible with cheap and abundant nitro-compounds by developing a cascade reduction process in which CO2 and nitro-compounds are reduced concurrently to yield N-methylamines with high monomethylation selectivity via the overall transfer of 12 electrons and 12 protons.

Electroactivated alkylation of amines with alcohols: Via both direct and indirect borrowing hydrogen mechanisms

Appiagyei, Benjamin,Bhatia, Souful,Keeney, Gabriela L.,Dolmetsch, Troy,Jackson, James E.

supporting information, p. 860 - 869 (2020/02/21)

A green, efficient N-alkylation of amines with simple alcohols has been achieved in aqueous solution via an electrochemical version of the so-called "borrowing hydrogen methodology". Catalyzed by Ru on activated carbon cloth (Ru/ACC), the reaction works well with methanol, and with primary and secondary alcohols. Alkylation can be accomplished by either of two different electrocatalytic processes: (1) in an undivided cell, alcohol (present in excess) is oxidized at the Ru/ACC anode; the aldehyde or ketone product condenses with the amine; and the resulting imine is reduced at an ACC cathode, combining with protons released by the oxidation. This process consumes stoichiometric quantities of current. (2) In a membrane-divided cell, the current-activated Ru/ACC cathode effects direct C-H activation of the alcohol; the resulting carbonyl species, either free or still surface-adsorbed, condenses with amine to form imine and is reduced as in (1). These alcohol activation processes can alkylate primary and secondary aliphatic amines, as well as ammonia itself at 25-70 °C and ambient pressure.

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