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1445-73-4

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1445-73-4 Usage

Chemical Properties

clear yellow to orange liquid

Uses

1-Methyl-4-piperidone, are widely used in artificial fibre industry. They are polymerizable and used as nylon precursors. They have excellent applications as solvents and as intermediates for organic synthesis. They are used in the aqueous carrier medium and amide penetrants in inks and water soluble paints.

Application

N-Methyl-4-piperidone can be used as a reactant to prepare:Spiropiperidine rings by reacting with malononitrile and electrophiles or Michael acceptors.(3E,5E)-1-Methyl-3,5-bis(phenylmethylene)-4-piperidinone by reacting with benzaldehyde via Michael addition, followed by intramolecular?O-cyclization/elimination sequential reactions.N,N′-Dimethylbispidinone by utilizing a double Mannich condensation method.

Preparation

[JACS (1948) vol 70 p 1820] for the synthesis of 1-methyl-4-piperidone: To a one-liter flask containing 350 ml of 20 % hydrochloric acid was added 86 g. of 1-methyl-3-carbethoxy-4-piperidone hyrdrochloride. After refluxing for one hour, the ferric chloride reagent gave no coloration. The solution was evaporated to dryness on a steam-bath at 10 mm. pressure. The solid product, heated at 100 °C for 4 hours at 0.1 mm and further dried over solid KOH for 24 hours, weighed 57.7 g, m.p. 80 - 120 °C.Although this melting range goes above that of the pure comound 0.45 of crude material dissolved in 90 ml. of hot acetone gave 0.40 g of pure compoundd melting at 93 - 95 °C. Other samples of crude piperidone hydrochloride showed even higher melting points than the one mentioned above, yet this apperently impure material always gave good yields of sharp melting product when recrystallized.

Purification Methods

It is best purified by fractional distillation The hydrochloride of the hydrate (4-diol) has m 94.7-95.5o, but the anhydrous hydrochloride which crystallises from CHCl3/Et2O has m 165-168o (164-167o) and can also be obtained by sublimation at 120o/2mm. The oxime has m 130-132o (from Me2CO). The methiodide crystallises from MeOH, the crystals with 1MeOH have m 189-190o, and the solvent-free iodide has m 202-204o(dec). [Lyle et al. J Org Chem 24 342 1959, Bowden & Greeen J Chem Soc 1164 1952, Tomita Yakugaku Zasshi (J Pharm Soc Japan) 71 1053 1951, Beilstein 21 IIII/IV 3183, 21/6 V 419.]

Check Digit Verification of cas no

The CAS Registry Mumber 1445-73-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,4 and 5 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1445-73:
(6*1)+(5*4)+(4*4)+(3*5)+(2*7)+(1*3)=74
74 % 10 = 4
So 1445-73-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H11NO/c1-7-4-2-6(8)3-5-7/h2-5H2,1H3/p+1

1445-73-4 Well-known Company Product Price

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  • Alfa Aesar

  • (A13352)  1-Methyl-4-piperidone, 98%   

  • 1445-73-4

  • 50g

  • 520.0CNY

  • Detail
  • Alfa Aesar

  • (A13352)  1-Methyl-4-piperidone, 98%   

  • 1445-73-4

  • 100g

  • 847.0CNY

  • Detail
  • Alfa Aesar

  • (A13352)  1-Methyl-4-piperidone, 98%   

  • 1445-73-4

  • 250g

  • 1990.0CNY

  • Detail
  • Alfa Aesar

  • (A13352)  1-Methyl-4-piperidone, 98%   

  • 1445-73-4

  • 1000g

  • 6291.0CNY

  • Detail
  • Aldrich

  • (130036)  N-Methyl-4-piperidone  97%

  • 1445-73-4

  • 130036-5ML

  • 348.66CNY

  • Detail
  • Aldrich

  • (130036)  N-Methyl-4-piperidone  97%

  • 1445-73-4

  • 130036-100ML

  • 1,242.54CNY

  • Detail
  • Aldrich

  • (130036)  N-Methyl-4-piperidone  97%

  • 1445-73-4

  • 130036-500ML

  • 4,496.31CNY

  • Detail

1445-73-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Methyl-4-piperidone

1.2 Other means of identification

Product number -
Other names 1-Methylpiperid-4-one

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:1445-73-4 SDS

1445-73-4Synthetic route

N-methyl-4-hydroxypiperidine
106-52-5

N-methyl-4-hydroxypiperidine

1-Methyl-4-piperidone
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%
methylamine
74-89-5

methylamine

benzene
71-43-2

benzene

1-Methyl-4-piperidone
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%
1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester
13221-89-1, 56026-45-0

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

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With hydrogenchloride; water
ethyl 1-methyl-4-oxo-piperidin-3-carboxylate
25012-72-0

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

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With hydrogenchloride; water
1,5-dichloropentan-3-one
3592-25-4

1,5-dichloropentan-3-one

methylamine
74-89-5

methylamine

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With ethanol; water; sodium carbonate
4-Methoxy-1-methyl-piperidin-4-ol
76360-18-4

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

A

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

B

methanol
67-56-1

methanol

Conditions
ConditionsYield
Product distribution; equilibrium, determination by 13C NMR;
2-(1-Methyl-piperidin-4-ylideneamino)-propionamide
142080-50-0

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

A

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

B

alanine amide
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

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

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

l-methyl-piperidin-4-ol

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With potassium permanganate; sulfuric acid; water
N,N-dimethyl-4-oxopiperidinium sulfate

N,N-dimethyl-4-oxopiperidinium sulfate

methylamine
74-89-5

methylamine

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

3,3'-methylimino-di-propionic acid diethyl ester
6315-60-2

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

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaH; benzene
2: water; hydrochloric acid
View Scheme
3-methyl[(3-methoxy-3-oxopropyl)methylamino]propanoate
105-71-5

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

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

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

1,2-dimethoxybenzene

A

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

B

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

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

Glycine ethyl ester isocyanate
2949-22-6

Glycine ethyl ester isocyanate

A

1-Methyl-4-piperidone
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

4-piperidone hydrochloride
41979-39-9

4-piperidone hydrochloride

methyl iodide
74-88-4

methyl iodide

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With potassium carbonate In ethanol for 2h; Reflux;
1-methyl-4-oxo-piperidine-3-carboxylic acid ethyl ester; hydrochloride
15637-49-7

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

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

Conditions
ConditionsYield
With potassium hydroxide
piperidin-4-one
41661-47-6

piperidin-4-one

methyl iodide
74-88-4

methyl iodide

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

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

1-Methyl-4-piperidone

1,1-dimethylhydrazine
57-14-7

1,1-dimethylhydrazine

1-methyl-4-piperidone dimethylhydrazone
136415-15-1

1-methyl-4-piperidone dimethylhydrazone

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

1-Methyl-4-piperidone

benzene
71-43-2

benzene

Medipine
31309-39-4

Medipine

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

1-Methyl-4-piperidone

5-chloro-1H-indole
17422-32-1

5-chloro-1H-indole

5-chloro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-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;
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

1-methyl-4-aminopiperidine
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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

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

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

1-benzyl-4-(1-methyl-piperidin-4-yl)-piperazine-2-carboxylic acid ethyl ester
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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

ethyl 2-O-dimethylsilane-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
1180492-09-4

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

ethyl 2-O-[4-(dimethylsilyloxy)-1-methylpiperidine]-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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

(2-aminoethyl)methylcarbamic acid tert-butyl ester
121492-06-6

(2-aminoethyl)methylcarbamic acid tert-butyl ester

methyl[2-(1-methylpiperidin-4-ylamino)ethyl]carbamic 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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

p-methoxyphenylisocyanide
10349-38-9

p-methoxyphenylisocyanide

2-amino-phenol
95-55-6

2-amino-phenol

2-(4-(benzo[d]oxazol-2-yl)-1-methylpiperidin-4-ylamino)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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

methyl iodide
74-88-4

methyl iodide

N,N-dimethyl-4-oxopiperidinium 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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine
147081-44-5

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

(S)-3-(1-methyl-piperidin-4-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester
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%
tert-butyl (R)-3-(aminomethyl)pyrrolidine-1-carboxylate
199174-29-3

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

1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

(R)-3-[(1-methyl-piperidin-4-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

tryptamine
61-54-1

tryptamine

(E)-but-2-enoic acid
107-93-7

(E)-but-2-enoic acid

tert-butylisonitrile
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

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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

5-chloro-pyridin-2-yl hydrazine
27032-63-9

5-chloro-pyridin-2-yl hydrazine

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

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

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

1-Methyl-4-piperidone

4-(Methylthio)benzaldehyde
3446-89-7

4-(Methylthio)benzaldehyde

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

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

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

1-Methyl-4-piperidone

C17H16N4O

C17H16N4O

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

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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

C17H16N4O2

C17H16N4O2

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

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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

dimethyl sulfate
77-78-1

dimethyl sulfate

1,1-dimethyl-4-oxopiperidinium methylsulfate
193337-36-9

1,1-dimethyl-4-oxopiperidinium methylsulfate

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

1-Methyl-4-piperidone

3-bromo-1-methylpiperidin-4-one hydrobromide
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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

aniline
62-53-3

aniline

N-(1-methyl-4-piperidinyl)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
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

1-methyl-N-(4-methylbenzyl)-piperidin-4-amine
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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

1-methyl-N-(4-methylbenzyl)-piperidin-4-amine
359878-18-5

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

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

1-Methyl-4-piperidone

potassium cyanide

potassium cyanide

ammonium carbonate
506-87-6

ammonium carbonate

8-methyl-1,3,8-triazaspiro<4.5>decane-2,4-dione
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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

2,6-dichlorobenzaldehyde
83-38-5

2,6-dichlorobenzaldehyde

thiourea
17356-08-0

thiourea

(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
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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

thiourea
17356-08-0

thiourea

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

(E)-6-methyl-8-(2-methylbenzylidene)-4-o-tolyl-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione
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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

thiourea
17356-08-0

thiourea

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

(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
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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

(E)-3-(2-furanyl)-2-propenal
39511-08-5

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

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

(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%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

C16H14N4O
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

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%

1445-73-4Relevant articles and documents

Phosphinous Acid Platinum Complex as Robust Catalyst for Oxidation: Comparison with Palladium and Mechanistic Investigations

Membrat, Romain,Vasseur, Alexandre,Martinez, Alexandre,Giordano, Laurent,Nuel, Didier

, p. 5427 - 5434 (2018)

Secondary phosphine oxides proved to be effective preligands to stabilise a hydroxy-platinum based catalyst that allows the aerobic/anaerobic oxidation of challenging substrates. Kinetic comparisons showed that this system is more efficient and stable than previously reported similar palladium-based catalysts. A neutral platinum dimer bearing bridging hydroxy ligands has been isolated and fully characterised by X-ray diffraction and its involvement in the mechanism has been evidenced by mechanistic studies.

-

Essery et al.

, p. 1142,1147 (1963)

-

Method for synthesizing (S N-) methylpiperidone -4-piperidone (piperidone-methylpiperidone) (by machine translation)

-

Paragraph 0027-0056, (2019/12/02)

The synthesis method comprises the following steps N - taking 1,3 - formaldehyde, diethylacetonate, and methylamine as raw materials, carrying out reaction under the catalytic conditions of the catalyst, generating an intermediate product, and carrying out decarboxylation N - reaction, and the methyl-4-piperidone is obtained. The synthesis method has the advantages of simple operation, short production process, high raw material conversion rate, lower production cost and higher economic benefit. (by machine translation)

Synthesis and antiproliferative activity of cyclic arylidene ketones: a direct comparison of monobenzylidene and dibenzylidene derivatives

Huber, Imre,Zupk, Istvn,Kovcs, Ida J.,Minorics, Renta,Gulys-Fekete, Gergely,Masz, Gbor,Perjsi, Pl

, p. 973 - 981 (2015/02/19)

Abstract To give further insight into the influence of the structural modifications of enones and dienones on their antiproliferative properties, 25 derivatives of enones: (E)-2-benzylidene-1-cyclohexanones, (E)-2-benzylidene-1-tetralones, (E)-2-benzylidene-1-indanone, and dienones: (E,E)-2,5- or 2,6-dibenzylidene-1-cyclanones, (E,E)-3,5-dibenzylidene-4-piperidones were synthesized using a newly developed "one-pot" synthetic method. Due to the fact that all of them have the same aryl substituents (phenyl or 4-chlorophenyl) in the arylidene moiety, it is possible to compare the relevant contribution of the single-point structural modifications (type of ring or N-substitution) on their potency on the basis of their IC 50 values. Their antiproliferative activity was evaluated against the following four human adherent cancer cell lines: HeLa, A431, A2780, and MCF7. The cytotoxicity screen has revealed that the dibenzylidene dienones in general dominate the monobenzylidene enones in this respect. The nitrogen-containing heterocyclic dienones at the same time displayed higher inhibitory properties toward these human carcinoma cell lines compared with their homocyclic dienone analogs. One of the eight newly prepared 4-piperidone derivatives, N-(γ-oxobutyl)-(E,E)-3,5-bis(p-chlorobenzylidene)-4-piperidone is as potent a cell growth inhibitor (IC 50 of 0.438-1.409 μM) as the N-methyl-(E,E)-3,5-bis(p-chlorobenzylidene)-4-piperidone (IC 50 of 0.447-1.048 μM), one of the most active among the previously described compounds in this series. Catalytic hydrogen-transfer isomerization of compounds with two exocyclic benzylidene double bonds to derivatives with endocyclic double bonds results in the complete loss of antiproliferative activity. The structural modifications and 50 % inhibitory concentration (IC 50) values resulted in correlations which can promote the design of more potent derivatives of the 4-piperidone dienones.

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