1-Methyl-4-piperidone

Base Information

• Chemical Name: 1-Methyl-4-piperidone
• CAS No.: 1445-73-4
• Molecular Formula: C6H11NO
• Molecular Weight: 113.159
• Hs Code.: 29333999
• European Community (EC) Number: 215-895-5
• NSC Number: 66491
• DSSTox Substance ID: DTXSID20162735
• Nikkaji Number: J86.542G
• Wikidata: Q72495992
• Mol file: 1445-73-4.mol

Synonyms:1-methyl-4-piperidone

Chemical Property of 1-Methyl-4-piperidone

Chemical Property:

• Appearance/Colour: clear yellow to orange liquid
• Vapor Pressure: 0.85mmHg at 25°C
• Melting Point: 192-193 °C(Solv: ethyl acetate (141-78-6))
• Refractive Index: 1.460 - 1.462
• Boiling Point: 181.5 °C at 760 mmHg
• PKA: 8.02±0.20(Predicted)
• Flash Point: 60 °C
• PSA: 20.31000
• Density: 0.992 g/cm³
• LogP: 0.21900
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Water Solubility.: MISCIBLE
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 113.084063974
• Heavy Atom Count: 8
• Complexity: 90.7

Purity/Quality:

99% ^*data from raw suppliers

1-Methyl-4-piperidone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-10-36/37/38
• Safety Statements: 23-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CN1CCC(=O)CC1
• 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.

Technology Process of 1-Methyl-4-piperidone

There total 19 articles about 1-Methyl-4-piperidone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

N-methyl-4-hydroxypiperidine (106-52-5) → 1-Methyl-4-piperidone (1445-73-4)

Guidance literature:

With dmap; [2,2]bipyridinyl; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; copper(l) chloride; In acetonitrile; at 20 ℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time; chemoselective reaction;

DOI:10.1002/anie.201309634

Reference yield: 91.7%

methylamine (74-89-5) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 1-Methyl-4-piperidone (1445-73-4)

Guidance literature:

methylamine; benzene; With formaldehyd; toluene-4-sulfonic acid; diethyl 1,3-acetonedicarboxylate; Reflux;

With hydrogenchloride; In water; for 4h; Time;

Reference yield:

1,2-dimethoxybenzene (91-16-7) → 1-Methyl-4-piperidone (1445-73-4) + 4-(2,3-Dimethoxyphenyl)-1,2,3,6-tetrahydro-1-methyl-pyridine (82359-63-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran;

upstream raw materials:

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

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

1,5-dichloropentan-3-one

methylamine

Downstream raw materials:

4,4-bis-(4-hydroxy-3,5-dimethyl-phenyl)-1-methyl-piperidine

8-methyl-2r,3c-diphenyl-1,4-dioxa-8-aza-spiro[4.5]decane

1-(1-methyl-[4]piperidylidenamino)-3,3-diphenyl-azetidine-2,4-dione

2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamidine; dihydrochloride

Refernces

Probes for narcotic receptor mediated phenomena: Synthesis of rac-(3R,6aS,11aR)-1,3,4,5,6,11a-hexahydro-2-methyl- 2H-3,6a-methanobenzofuro[2,3-c]azocin-8-ol, an epoxy isomer of 5-phenylmorphan

10.1002/hlca.200390048

The study focuses on synthesizing and analyzing epoxy isomers of 5-phenylmorphan compounds to explore their conformational requirements for opioid receptor binding and pharmacological activity. Specifically, it reports the synthesis of the para-d isomer, rac-(3R,6aS,11aR)-1,3,4,5,6,11a-hexahydro-2-methyl-2H-3,6a-methanobenzofuro[2,3-c]azocin-8-ol. The process involved constructing the 5-phenylazabicyclo[3.3.1]nonane skeleton and forming an epoxy bridge to restrict the rotation of the phenyl ring. 1-Methylpiperidin-4-one was used as a starting material for constructing the azabicyclo skeleton.