71322-99-1

Basic information

• Product Name: 2-Methyl-4-piperidone
• Synonyms: 2-METHYL-4-PIPERIDONE;2-METHYL-PIPERIDIN-4-ONE;2-Methyl-4-piperdone;2-Methyl-4-piperidinone;4-Piperidinone, 2-methyl-
• CAS NO: 71322-99-1
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.16
• Mol File: 71322-99-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 182.6 °C at 760 mmHg
• Flash Point: 81.8 °C
• Appearance: /
• Density: 0.951 g/cm³
• Vapor Pressure: 0.803mmHg at 25°C
• Refractive Index: 1.438
• Storage Temp.: 2-8°C
• PKA: 9.01±0.40(Predicted)
• CAS DataBase Reference: 2-Methyl-4-piperidone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-4-piperidone(71322-99-1)
• EPA Substance Registry System: 2-Methyl-4-piperidone(71322-99-1)

Safety Data

• Hazardous Substances Data: 71322-99-1(Hazardous Substances Data)

Usage

General Description

2-Methyl-4-piperidone, also known as 2-Methyl-4-piperidinone, is a chemical compound with the molecular formula C6H11NO. It is a cyclic amide that is commonly used as a precursor in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is a colorless liquid with a slightly amine-like odor, and it is soluble in water, ethanol, and most organic solvents. 2-Methyl-4-piperidone is a versatile intermediate in organic synthesis, and it is commonly used in the production of various pharmaceuticals, including analgesics, antihistamines, and psychiatric medications. Additionally, it is also utilized in the manufacture of insecticides, herbicides, and other agrochemicals. Due to its diverse range of applications, 2-Methyl-4-piperidone is an important compound in the field of organic chemistry and chemical industry.

InChI:InChI=1/C6H11NO/c1-5-4-6(8)2-3-7-5/h5,7H,2-4H2,1H3

Synthetic route

7-methyl-8-(tert-butoxycarbonyl)-1,4-dioxo-8-azaspiro[4,5]decane (325486-40-6) → 2-methyl-4-oxopiperidine (71322-99-1)

Conditions	Yield
Stage #1: 7-methyl-8-(tert-butoxycarbonyl)-1,4-dioxo-8-azaspiro[4.5]decane With trifluoroacetic acid at 0 - 5℃; for 0.166667h; Stage #2: With water for 2.5h; Heating / reflux;	71.3%

N-Boc-7-methyl-1,4-dioxa-8-azaspiro<4.5>decane (126503-08-0) → 2-methyl-4-oxopiperidine (71322-99-1)

Conditions	Yield
Stage #1: N-Boc-7-methyl-1,4-dioxa-8-azaspiro<4.5>decane With trifluoroacetic acid at 0 - 5℃; for 0.166667h; Stage #2: With water for 2.5h; Heating / reflux;	71.3%
Stage #1: N-Boc-7-methyl-1,4-dioxa-8-azaspiro<4.5>decane With hydrogenchloride; water In acetic acid at 20℃; Stage #2: With sodium hydroxide In water

(+-)-1,5-dimethoxy-hexan-3-one → 2-methyl-4-oxopiperidine (71322-99-1)

Conditions	Yield
With ammonia; water

benzyl 2-methyl-4-oxopiperidine-1-carboxylate (849928-34-3) → 2-methyl-4-oxopiperidine (71322-99-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 760 Torr; for 12h;

4-methoxypyridine (620-08-6) → 2-methyl-4-oxopiperidine (71322-99-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 50 percent / tetrahydrofuran / 2 h / -25 °C 2: 80 percent / Zn; AcOH / 12 h / 80 °C 3: H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

3,4-dihydro-2-methyl-4-oxo-1(2H)-pyridinecarboxylic acid phenylmethyl ester (190906-91-3) → 2-methyl-4-oxopiperidine (71322-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / Zn; AcOH / 12 h / 80 °C 2: H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

2-methyl-piperidin-4-one hydrochloride → 2-methyl-4-oxopiperidine (71322-99-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0℃;
With hydrogenchloride In water for 14.5h; Heating / reflux;

7-methyl-1,4-dioxa-8-azaspiro[4.5]decane (676490-94-1) → 2-methyl-4-oxopiperidine (71322-99-1)

Conditions	Yield
With water; trifluoroacetic acid at 0℃; for 2.5h; Heating / reflux;

di-tert-butyl dicarbonate (24424-99-5) + sec.-butyllithium (598-30-1) + 4,4-ethylenedioxy-piperidine (177-11-7) → 2-methyl-4-oxopiperidine (71322-99-1)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid In tetrahydrofuran; cyclohexane; water; ethyl acetate

Upstream product

• 849928-34-3 benzyl 2-methyl-4-oxopiperidine-1-carboxylate 
• 620-08-6 4-methoxypyridine 
• 190906-91-3 3,4-dihydro-2-methyl-4-oxo-1(2H)-pyridinecarboxylic acid phenylmethyl ester 
• 13729-77-6 2-methyl-piperidin-4-one hydrochloride 
• 325486-40-6 7-methyl-8-(tert-butoxycarbonyl)-1,4-dioxo-8-azaspiro[4.5]decane 
• 126503-08-0 N-Boc-7-methyl-1,4-dioxa-8-azaspiro<4.5>decane 
• 676490-94-1 7-methyl-1,4-dioxa-8-azaspiro[4.5]decane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 598-30-1 sec.-butyllithium 
• 177-11-7 4,4-ethylenedioxy-piperidine 

Downstream Products

• 190906-92-4 tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate 
• 790667-43-5 (2R)-2-methyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 790667-49-1 (S)-2-methyl-4-oxopiperidine-1-carboxylic acid tert-butyl ester 
• 344329-35-7 2-methyl-piperidin-4-ol 

Relevant articles and documents

Discovery of potent and selective inhibitors of 11β-HSD1 for the treatment of metabolic syndrome

High throughput screening efforts have identified a novel class of dichloroaniline amide 11β-HSD1 inhibitors. SAR studies initiated from dichloroaniline 4 focused on retaining the potency and selectivity profile of the lead.

Indole, azaindole and related heterocyclic 4-alkenyl piperidine amides

This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with new piperidine 4-alkenyl derivatives that possess unique antiviral activity. More particularly, the present invention relates to compounds useful for the treatment of HIV and AIDS. The compounds of the invention for the general Formula I: wherein: Z is Q is selected from the group consisting of: —W— is

Indole, azaindole and related heterocyclic 4-alkenyl piperidine amides

This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with new piperidine 4-alkenyl derivatives that possess unique antiviral activity. More particularly, the present invention relates to compounds useful for the treatment of HIV and AIDS. The compounds of the invention for the general Formula I: wherein: Z is Q is selected from the group consisting of: —W— is