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1445-73-4

Basic Information
CAS No.: 1445-73-4
Name: 1-Methyl-4-piperidone
Molecular Structure:
Molecular Structure of 1445-73-4 (1-Methyl-4-piperidone)
Formula: C6H11NO
Molecular Weight: 113.16 .
Synonyms: 4-Piperidone,1-methyl- (6CI,7CI,8CI);1-Methyl-4-oxopiperidine;N-Methyl-4-piperidinone;NSC66491;4-Piperidinone,1-methyl-;N-Methyl-4-piperidone;
EINECS: 215-895-5
Density: 0.992 g/cm3
Melting Point: 192-193 °C(Solv: ethyl acetate (141-78-6))
Boiling Point: 181.5 °C at 760 mmHg
Flash Point: 60 °C
Solubility: miscible with water
Appearance: clear yellow to orange liquid
Hazard Symbols: CorrosiveC,IrritantXi
Risk Codes: 34-10-36/37/38
Safety: 23-24/25-37/39-26
Transport Information: UN 1224 3/PG 3
PSA: 20.31000
LogP: 0.21900
Synthetic route
106-52-5

N-methyl-4-hydroxypiperidine

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With dmap; [2,2]bipyridinyl; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; copper(l) chloride In acetonitrile at 20℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time; chemoselective reaction;96%
With di-μ-chlorotetrakys-[(RP)-tert-butylphenylphosphinito-κ-P]diplatinate(2-); methyl vinyl ketone; sodium hydroxide In water; toluene for 16h; Schlenk technique; Inert atmosphere; Heating;14%
74-89-5

methylamine

71-43-2

benzene

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
Stage #1: methylamine; benzene With formaldehyd; toluene-4-sulfonic acid; diethyl 1,3-acetonedicarboxylate Reflux;
Stage #2: With hydrogenchloride In water for 4h; Time;
91.7%
13221-89-1, 56026-45-0

1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With hydrogenchloride; water
25012-72-0

ethyl 1-methyl-4-oxo-piperidin-3-carboxylate

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With hydrogenchloride; water
3592-25-4

1,5-dichloropentan-3-one

74-89-5

methylamine

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With ethanol; water; sodium carbonate
76360-18-4

4-Methoxy-1-methyl-piperidin-4-ol

A

1445-73-4

1-Methyl-4-piperidone

B

67-56-1

methanol

Conditions
ConditionsYield
Product distribution; equilibrium, determination by 13C NMR;
142080-50-0

2-(1-Methyl-piperidin-4-ylideneamino)-propionamide

A

1445-73-4

1-Methyl-4-piperidone

B

4726-84-5

alanine amide

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 34℃; Rate constant; var. temp.;
4-benzoyloxy-1-methyl-1,2,3,6-tetrahydro-pyridine

4-benzoyloxy-1-methyl-1,2,3,6-tetrahydro-pyridine

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With hydrogenchloride; water
l-methyl-piperidin-4-ol

l-methyl-piperidin-4-ol

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With potassium permanganate; sulfuric acid; water

N,N-dimethyl-4-oxopiperidinium sulfate

74-89-5

methylamine

1445-73-4

1-Methyl-4-piperidone

6315-60-2

3,3'-methylimino-di-propionic acid diethyl ester

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaH; benzene
2: water; hydrochloric acid
View Scheme
105-71-5

3-methyl[(3-methoxy-3-oxopropyl)methylamino]propanoate

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium; xylene
2: water; hydrochloric acid
View Scheme
91-16-7

1,2-dimethoxybenzene

A

1445-73-4

1-Methyl-4-piperidone

B

82359-63-5

4-(2,3-Dimethoxyphenyl)-1,2,3,6-tetrahydro-1-methyl-pyridine

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran

9-methyl-4-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-1-thia-4,9-diazaspiro[5.5]-undecane-5-carboxamide

2949-22-6

Glycine ethyl ester isocyanate

A

1445-73-4

1-Methyl-4-piperidone

B

9-Methyl-4-{[4-(2-Butynyloxy)Phenyl]Sulfonyl}-N-Hydroxy-1-Thia-4,9-Diazaspirol[5.5]Undecane-5-Carboxamide

9-Methyl-4-{[4-(2-Butynyloxy)Phenyl]Sulfonyl}-N-Hydroxy-1-Thia-4,9-Diazaspirol[5.5]Undecane-5-Carboxamide

41979-39-9

4-piperidone hydrochloride

74-88-4

methyl iodide

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With potassium carbonate In ethanol for 2h; Reflux;
15637-49-7

1-methyl-4-oxo-piperidine-3-carboxylic acid ethyl ester; hydrochloride

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With potassium hydroxide
41661-47-6

piperidin-4-one

74-88-4

methyl iodide

1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With potassium carbonate In ethanol for 3h; Reflux;
1445-73-4

1-Methyl-4-piperidone

57-14-7

1,1-dimethylhydrazine

136415-15-1

1-methyl-4-piperidone dimethylhydrazone

Conditions
ConditionsYield
With acetic acid In diethyl ether at 20℃; for 12h;100%
1445-73-4

1-Methyl-4-piperidone

71-43-2

benzene

31309-39-4

Medipine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 20℃; for 3h;100%
With aluminium trichloride at 60℃; for 2h; Yield given;
1445-73-4

1-Methyl-4-piperidone

17422-32-1

5-chloro-1H-indole

109793-84-2

5-chloro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Conditions
ConditionsYield
With potassium hydroxide In methanol for 8.5h; Heating;100%
With pyrrolidine In ethanol Heating;
1445-73-4

1-Methyl-4-piperidone

41838-46-4

1-methyl-4-aminopiperidine

Conditions
ConditionsYield
With ammonium formate; palladium on carbon In methanol100%
With ammonium formate; palladium on activated charcoal In methanol; water at 20℃;75%
With ammonium formate; palladium on activated charcoal In methanol; water at 20℃;37%
1445-73-4

1-Methyl-4-piperidone

1-benzyl-piperazine-2-carboxylic acid ethyl ester bis(trifluoroacetate)

688020-31-7

1-benzyl-4-(1-methyl-piperidin-4-yl)-piperazine-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃;100%
1445-73-4

1-Methyl-4-piperidone

1180492-09-4

ethyl 2-O-dimethylsilane-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

1180492-18-5

ethyl 2-O-[4-(dimethylsilyloxy)-1-methylpiperidine]-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Conditions
ConditionsYield
With titanium(IV) isopropylate; bis(1,5-cyclooctadiene)nickel(0); potassium tert-butylate; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;100%
1445-73-4

1-Methyl-4-piperidone

121492-06-6

(2-aminoethyl)methylcarbamic acid tert-butyl ester

919834-58-5

methyl[2-(1-methylpiperidin-4-ylamino)ethyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 1-Methyl-4-piperidone; (2-aminoethyl)methylcarbamic acid tert-butyl ester With sodium tris(acetoxy)borohydride In DCE at 20℃;
Stage #2: With methanol In dichloromethane pH=> 12;
100%
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 16h;55%
1445-73-4

1-Methyl-4-piperidone

10349-38-9

p-methoxyphenylisocyanide

95-55-6

2-amino-phenol

1572383-01-7

2-(4-(benzo[d]oxazol-2-yl)-1-methylpiperidin-4-ylamino)phenol

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 2,2,2-trifluoroethanol at 55℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;100%
1445-73-4

1-Methyl-4-piperidone

74-88-4

methyl iodide

26822-37-7

N,N-dimethyl-4-oxopiperidinium iodide

Conditions
ConditionsYield
In acetone99%
In acetone at 0 - 20℃; for 24h;99%
In acetone at 25 - 30℃; for 2h;98%
1445-73-4

1-Methyl-4-piperidone

147081-44-5

(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine

1010446-48-6

(S)-3-(1-methyl-piperidin-4-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With MP-triacetoxyborohydride In tetrahydrofuran at 20℃; for 42h; Not specified;99%
199174-29-3

tert-butyl (R)-3-(aminomethyl)pyrrolidine-1-carboxylate

1445-73-4

1-Methyl-4-piperidone

1010446-55-5

(R)-3-[(1-methyl-piperidin-4-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With MP-triacetoxyborohydride In tetrahydrofuran at 20℃; for 24h; Not specified;99%
1445-73-4

1-Methyl-4-piperidone

61-54-1

tryptamine

107-93-7

(E)-but-2-enoic acid

119072-55-8, 7188-38-7

tert-butylisonitrile

4-{(but-2-enoyl)-[2-(1H-indole-3-yl)ethyl]amino}-1-methylpiperidine-4-carboxylic acid tert-butylamide

Conditions
ConditionsYield
In methanol at 20℃; for 18h; Ugi reaction;99%
1445-73-4

1-Methyl-4-piperidone

27032-63-9

5-chloro-pyridin-2-yl hydrazine

1-methylpiperidin-4-one (5-chloropyridin-2-yl)hydrazone

Conditions
ConditionsYield
In ethanol for 0.5h; Reflux;99%
1445-73-4

1-Methyl-4-piperidone

3446-89-7

4-(Methylthio)benzaldehyde

3,5-Bis((E)-4-methylthiobenzylidene)-1-methylpiperidin-4-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; Aldol Condensation;99%
1445-73-4

1-Methyl-4-piperidone

C17H16N4O

3'-(3,4-dimethylphenyl)-1-methylspiro[piperidine-4,6'-[1,2,4]triazino[2,3-c]quinazolin]-2'(7'H)-one

Conditions
ConditionsYield
With acetic acid for 3h; Reflux;99%
1445-73-4

1-Methyl-4-piperidone

C17H16N4O2

3'-(4-ethoxyphenyl)-1-methylspiro[piperidine-4,6'-[1,2,4]triazino[2,3-c]quinazolin]-2'(7'H)-one

Conditions
ConditionsYield
With acetic acid for 3h; Reflux;99%
1445-73-4

1-Methyl-4-piperidone

77-78-1

dimethyl sulfate

193337-36-9

1,1-dimethyl-4-oxopiperidinium methylsulfate

Conditions
ConditionsYield
In acetone at 0℃; for 3h;98.7%
1445-73-4

1-Methyl-4-piperidone

89580-42-7

3-bromo-1-methylpiperidin-4-one hydrobromide

Conditions
ConditionsYield
With hydrogen bromide; bromine; acetic acid In water at 20 - 25℃; Large scale;98.3%
With hydrogen bromide; bromine; acetic acid In water at 20 - 25℃; Temperature;94.1%
1445-73-4

1-Methyl-4-piperidone

62-53-3

aniline

22261-94-5

N-(1-methyl-4-piperidinyl)aniline

Conditions
ConditionsYield
Stage #1: 1-Methyl-4-piperidone; aniline With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 0 - 20℃; for 16h;
Stage #2: With sodium hydroxide; water In 1,2-dichloro-ethane
98%
With sodium tetrahydroborate; molecular sieve 1) benzene, reflux, 20 h; 2) EtOH, room temp., 5 h; Yield given. Multistep reaction;
Stage #1: 1-Methyl-4-piperidone; aniline With acetic acid In methanol at 20℃; for 0.166667h;
Stage #2: With sodium cyanoborohydride In methanol
Stage #1: 1-Methyl-4-piperidone; aniline With acetic acid In methanol at 20℃; for 0.166667h;
Stage #2: With sodium cyanoborohydride In methanol
1445-73-4

1-Methyl-4-piperidone

359878-18-5

1-methyl-N-(4-methylbenzyl)-piperidin-4-amine

Conditions
ConditionsYield
Stage #1: 1-Methyl-4-piperidone With acetic acid In methanol for 0.0833333h; pH=5;
Stage #2: With sodium cyanoborohydride In methanol for 20h;
98%
1445-73-4

1-Methyl-4-piperidone

103-67-3

benzyl-methyl-amine

359878-18-5

1-methyl-N-(4-methylbenzyl)-piperidin-4-amine

Conditions
ConditionsYield
With NaCNBH3; sodium carbonate; acetic acid In methanol98%
1445-73-4

1-Methyl-4-piperidone

potassium cyanide

506-87-6

ammonium carbonate

52094-69-6

8-methyl-1,3,8-triazaspiro<4.5>decane-2,4-dione

Conditions
ConditionsYield
In methanol; water at 90℃; for 0.166667h; Bucherer-Bergs Reaction; Sealed tube; Microwave irradiation;98%
In methanol; water at 23℃; for 48h;51%
1445-73-4

1-Methyl-4-piperidone

83-38-5

2,6-dichlorobenzaldehyde

17356-08-0

thiourea

1310325-76-8

(E)-8-(2,6-dichlorobenzylidene)-4-(2,6-dichlorophenyl)-6-methyl-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione

Conditions
ConditionsYield
With sodium ethanolate at 20℃; Neat (no solvent);98%
1445-73-4

1-Methyl-4-piperidone

17356-08-0

thiourea

529-20-4

2-methylphenyl aldehyde

1310325-67-7

(E)-6-methyl-8-(2-methylbenzylidene)-4-o-tolyl-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione

Conditions
ConditionsYield
With sodium ethanolate at 20℃; Neat (no solvent);98%
1445-73-4

1-Methyl-4-piperidone

17356-08-0

thiourea

100-10-7

4-dimethylamino-benzaldehyde

1310325-65-5

(E)-8-(4-(dimethylamino)benzylidene)-4-(4-(dimethylamino)phenyl)-6-methyl-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione

Conditions
ConditionsYield
With sodium ethanolate at 20℃; Neat (no solvent);98%
1445-73-4

1-Methyl-4-piperidone

39511-08-5

(E)-3-(2-furanyl)-2-propenal

(3E,5E)-3,5-bis((E)-3-(furan-2-yl)allylidene)-1-methylpiperidin-4-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 20℃; for 24h; Inert atmosphere; Green chemistry;98%
1445-73-4

1-Methyl-4-piperidone

923757-23-7

C16H14N4O

1-methyl-3'-(4-methylphenyl)spiro[piperidine-4,6'-[1,2,4]triazino[2,3-c]quinazolin]-2'(7'H)-one

Conditions
ConditionsYield
With acetic acid for 3h; Reflux;98%
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    CAS:1445-73-4 1-Methyl-4-piperidone

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    1-Methyl-4-piperidone

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Chemistry

Molecular Structure of N-Methyl-4-piperidone (CAS NO.1445-73-4):

IUPAC Name: 1-Methylpiperidin-4-one
Canonical SMILES: CN1CCC(=O)CC1
InChI: InChI=1S/C6H11NO/c1-7-4-2-6(8)3-5-7/h2-5H2,1H3
InChIKey: HUUPVABNAQUEJW-UHFFFAOYSA-N
Molecular Weight: 113.15764 [g/mol]
Molecular Formula: C6H11NO
XLogP3-AA: -0.3
H-Bond Donor: 0
H-Bond Acceptor: 2 
Index of Refraction: 1.464
Molar Refractivity: 31.46 cm3
Molar Volume: 114 cm3
Surface Tension: 32.4 dyne/cm
Density: 0.992 g/cm3
Flash Point: 60 °C
Enthalpy of Vaporization: 41.77 kJ/mol
Boiling Point: 181.5 °C at 760 mmHg
Vapour Pressure: 0.85 mmHg at 25 °C
Appearance: clear yellow to orange liquid
storage temp.: 0-6 °C
Water Solubility: MISCIBLE
EINECS: 215-895-5
Product Categories: PHARMACEUTICAL INTERMEDIATES; Amines and Anilines; Carbonyl Compounds; Miscellaneous; Piperidines, Piperidones, Piperazines; Piperidine; Building Blocks; Heterocyclic Building Blocks; Piperidones

Safety Profile

Safety Information of N-Methyl-4-piperidone (CAS NO.1445-73-4):
Hazard Codes: CorrosiveC,IrritantXi
Risk Statements: 34-10-36/37/38 
R34:Causes burns. 
R10:Flammable. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-24/25-37/39-26 
S24/25:Avoid contact with skin and eyes.
S23:Do not breathe vapour. 
S37/39:Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 1224 3/PG 3
WGK Germany: 3
Hazard Note: Irritant
HazardClass: 3

Specification

 N-Methyl-4-piperidone (CAS NO.1445-73-4), its Synonyms are 4-Piperidinone,1-methyl- ; 1-Methyltetrahydropyridin-4(1H)-one- ; N-Methyl-4-piperidone ; 4-Piperidone,1-methyl- (6CI,7CI,8CI) .