4629-78-1

Basic information

• Product Name: 3-Methylpiperidin-4-one hydrochloride
• Synonyms: 3-METHYL-PIPERIDIN-4-ONE HYDROCHLORIDE;4-Piperidinone, 3-methyl-, hydrochloride (1:1);4-Piperidinone, 3-Methyl-, hydrochloride;3-METHYL-PIPERIDIN-4-ONE HCL;3-Methoxypiperidin-4-one hydrochloride
• CAS NO: 4629-78-1
• Molecular Formula: C₆H₁₁NO*ClH
• Molecular Weight: 149.62
• Mol File: 4629-78-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 176.5-177 °C
• Boiling Point: 224.6 °C at 760 mmHg
• Flash Point: 89.7 °C
• Appearance: /
• Vapor Pressure: 0.0738mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 3-Methylpiperidin-4-one hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylpiperidin-4-one hydrochloride(4629-78-1)
• EPA Substance Registry System: 3-Methylpiperidin-4-one hydrochloride(4629-78-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 4629-78-1(Hazardous Substances Data)

Usage

General Description

3-Methylpiperidin-4-one hydrochloride is a chemical compound often used in research and development within the pharmaceutical industry. It falls within the category of intermediates & fine chemicals and the subcategory of pharmaceuticals. Its chemical formula is C6H12ClNO and it is characterized by its white crystalline form. However, its handling requires caution due to its potential for skin irritation, eye damage, and respiratory irritation. Like all chemicals, it should be used and stored responsibly, with appropriate safety measures taken to prevent direct exposure.

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

Synthetic route

ethyl 1-benzoyl-3-methyl-4-oxo-3-piperidinecarboxylate (17038-84-5) → 3-methylpiperidine-4-one hydrochloride (4629-78-1)

Conditions	Yield
With hydrogenchloride for 72h; Heating;	72%

ethyl 1-benzoyl-4-oxo-3-piperidinecarboxylate (4451-86-9) → 3-methylpiperidine-4-one hydrochloride (4629-78-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / NaH / 1,2-dimethoxy-ethane / 40 h / 60 °C 2: 72 percent / aq. HCl / 72 h / Heating View Scheme

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate (181269-69-2) → 3-methylpiperidine-4-one hydrochloride (4629-78-1)

Conditions	Yield
With hydrogenchloride In ethanol; dichloromethane at 0 - 25℃;

3-methylpiperidine-4-one hydrochloride (4629-78-1) + phenoxyamine hydrochloride (6092-80-4) → 4-methyl-1,2,3,4-tetrahydro-benzo[4,5]furo[3,2-c]pyridine (43213-62-3)

Conditions	Yield
With hydrogenchloride In ethanol

3-methylpiperidine-4-one hydrochloride (4629-78-1) → rac-trans-3-methylpiperidin-4-ol

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate 1) MeOH, r.t., 0.5 h, 2) MeOH, r.t., 4 h; Yield given; Multistep reaction;

3-methylpiperidine-4-one hydrochloride (4629-78-1) → 1-(4-hydroxy-3-methylpiperidino)cyclohexanecarbonitrile

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) aq. NaOH, 2) NaBH4 / 1) MeOH, r.t., 0.5 h, 2) MeOH, r.t., 4 h 2: 93 percent / aq. HCl / 24 h / Ambient temperature View Scheme

3-methylpiperidine-4-one hydrochloride (4629-78-1) → (3S,4S)-3-Methyl-1-(1-thiophen-2-yl-cyclohexyl)-piperidin-4-ol

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) aq. NaOH, 2) NaBH4 / 1) MeOH, r.t., 0.5 h, 2) MeOH, r.t., 4 h 2: 93 percent / aq. HCl / 24 h / Ambient temperature 3: 71 percent / diethyl ether / Heating View Scheme

3-methylpiperidine-4-one hydrochloride (4629-78-1) + 1-[4,4'-difluorodiphenylmethoxy]-3-chloropropane (120737-98-6) → 1-[1-(4,4'-difluorodiphenylmethoxy)-propyl]-3-methylpiperidine-4-one

Conditions	Yield
With sodium iodide; potassium carbonate In water; acetonitrile

3-methylpiperidine-4-one hydrochloride (4629-78-1) + acetyl chloride (75-36-5) → 1-acetyl-3-methyl-piperidin-4-one (1228450-13-2)

Conditions	Yield
Stage #1: 3-methylpiperidine-4-one hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 0.5h; Stage #2: acetyl chloride In dichloromethane at 0℃; for 16h; Stage #3: With sodium hydrogencarbonate In dichloromethane; water

methyl 3-bromomethyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate + 3-methylpiperidine-4-one hydrochloride (4629-78-1) → methyl 6-[(1-methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1335116-95-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 22h;

C13H12ClF3N2O3S + 3-methylpiperidine-4-one hydrochloride (4629-78-1) → 3-ethyl-5-methyl-6-[(3-methyl-4-oxopiperidin-1-yl)carbonyl]-1-(3,3,3-trifluoropropyl)thieno[2,3-d]pyrimidin-2,4-(1H,3H)dione

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	236 mg

Upstream product

• 181269-69-2 tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate 
• 4451-86-9 ethyl 1-benzoyl-4-oxopiperidine-3-carboxylate 
• 17038-84-5 ethyl 1-benzoyl-3-methyl-4-oxo-3-piperidinecarboxylate 

Downstream Products

• 1335116-95-4 methyl 6-[(1-methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate 
• 36173-52-1 rac-trans-3-methylpiperidin-4-ol 

Relevant articles and documents

Pyrrolopyrazinyl Urea Kinase Inhibitors

The present invention relates to the use of novel pyrrolopyrazinyl urea derivatives of Formula I, wherein the variables R1, R2, R3, R4, and R5 are defined as described herein, which inhibit JAK and are useful for the treatment of auto-immune and inflammatory diseases.

The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum

With the aim of obtaining selective ligands of the low affinity binding sites of [3H]-1-[1-(2-thienyl)cyclohexyl]piperidine ([3H]TCP) in the rat cerebellum, oxygen and sulfur atoms were introduced in the TCP structure and derivatives to obtain analogues with a lowered lipophilicity. These compounds, and others already obtained, were assayed comparatively to determine their affinities for three sites labeled with [3H]TCP: one in the forebrain, the originally described PCP receptor, and two in the rat cerebellum. Lowering the lipophilicity and modifying the hetero-aromatic moiety yielded some ligands with increased affinity for the low affinity sites in the rat cerebellum and decreased affinity for the high affinity sites in the forebrain. Particularly, two compounds displaying both a high affinity and a good selectivity might be valuable tools to elucidate the pharmacology of the low affinity PCP sites labeled with [3H]TCP in the rat cerebellum.