931-20-4

Basic information

• Product Name: 1-METHYL-2-PIPERIDONE
• Synonyms: 1-methyl-2-piperidinon;1-Methyl-2-piperidinone;1-methyl-2-piperidon;1-Methylpiperidin-2-on;1-methyl-piperidin-2-one;1-Methylpiperidin-2-one;1-Methylpiperidine-2-one;2-Piperidone, 1-methyl-
• CAS NO: 931-20-4
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.16
• EINECS: 213-231-9
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Piperidones
• Mol File: 931-20-4.mol

Chemical Properties

• Boiling Point: 105-106 °C12 mm Hg(lit.)
• Flash Point: 196 °F
• Appearance: /
• Density: 1.029 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0762mmHg at 25°C
• Refractive Index: n20/D 1.482
• Storage Temp.: 2-8°C
• PKA: -0.41±0.20(Predicted)
• BRN: 1708
• CAS DataBase Reference: 1-METHYL-2-PIPERIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-2-PIPERIDONE(931-20-4)
• EPA Substance Registry System: 1-METHYL-2-PIPERIDONE(931-20-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: TO0124000
• F: 3-10
• Hazardous Substances Data: 931-20-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3098, 1949 DOI: 10.1021/ja01177a044Tetrahedron Letters, 29, p. 3049, 1988 DOI: 10.1016/0040-4039(88)85082-2

InChI:InChI=1/C6H11NO/c1-7-5-3-2-4-6(7)8/h2-5H2,1H3

Upstream product

• 675-20-7 piperidin-2-one 
• 77-78-1 dimethyl sulfate 
• 694-85-9 1-methyl-2-pyridone 
• 25077-25-2 N-methyladipinimide 
• 21382-30-9 5-(methylamino)pentanoic acid 
• 41880-29-9 5-methylamino-valeric acid ethyl ester 
• 105-39-5 chloroacetic acid ethyl ester 
• 74-88-4 methyl iodide 
• 13070-07-0 1-methylpiperidine-2-thione 
• 626-67-5 N-methylcyclohexylamine 
• 54105-23-6 1,1'-Dimethyl-3-(2'-piperidyl)-1,4,5,6-tetrahydropyridin 
• 68116-79-0 N-(chloromethyl)-2-piperidinone 
• 1066-35-9 dimethylmonochlorosilane 
• 6602-66-0 (1-methyl-piperidin-2-yl)-phenyl-methanone 

Downstream Products

• 91566-93-7 N-Methyl-3-nicotinoyl-piperidon-(2) 
• 34893-51-1 meso-1,3-bis-(1-methyl-[2]piperidyl)-acetone 
• 18747-42-7 N-methylpelletierine 
• 61170-35-2 6-(4-methoxy-phenyl)-1-methyl-1,2,3,4-tetrahydro-pyridine 
• 13070-07-0 1-methylpiperidine-2-thione 
• 30609-85-9 1-methyl-6-phenyl-1,2,3,4-tetrahydropyridine 
• 107202-92-6 6-benzyl-1-methyl-1,2,3,4-tetrahydro-pyridine 
• 101113-68-2 (+/-)-sedaminone 
• 89855-60-7 5-(dimethylamino)pentanoic acid 
• 152581-76-5 [1-Methyl-piperidin-(2E)-ylidene]-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amine 
• 154207-41-7 1-Methyl-3-(trifluoroacetyl)-piperidin-2-one 
• 155398-07-5 1-methyl-3-(1-hydroxy-2,2,2-trifluoroethylidene)-2-piperidone 
• 1690-76-2 1,3-dimethyl-2-piperidinone 
• 125133-94-0 N-methylconiine 

Relevant articles and documents

Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride

We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation-deprotonation as the preferred reaction pathway.

Aerobic Oxidation of Cyclic Amines to Lactams Catalyzed by Ceria-Supported Nanogold

Abstract: The oxidative transformation of cyclic amines to lactams, which are important chemical feedstocks, is efficiently catalyzed by CeO2-supported gold nanoparticles (Au/CeO2) and Aerosil 200 in the presence of an atmosphere of O2. The complete conversion of pyrrolidine was achieved in 6.5?h at 160 °C, affording a 97 % yield of the lactam product 2-pyrrolidone (γ-butyrolactam), while 2-piperidone (δ-valerolactam) was synthesized from piperidine (83 % yield) in 2.5?h. Caprolactam, the precursor to the commercially important nylon-6, was obtained from hexamethyleneimine in 37 % yield in 3?h. During the oxidation of pyrrolidine, two transient species, 5-(pyrrolidin-1-yl)-3,4-dihydro-2H-pyrrole (amidine-5) and 4-amino-1-(pyrrolidin-1-yl)butan-1-one, were observed. Both of these compounds were oxidized to 2-pyrrolidone under catalytic conditions, indicating their role as intermediates in the reaction pathway. In addition to the reactions of cyclic secondary amines, Au/CeO2 also efficiently catalyzes the oxidation of N-methyl cyclic tertiary amines to the corresponding lactams at 80 and 100 °C. Graphical Abstract: [Figure not available: see fulltext.]

Supported Gold Nanoparticles for Efficient α-Oxygenation of Secondary and Tertiary Amines into Amides

Although the α-oxygenation of amines is a highly attractive method for the synthesis of amides, efficient catalysts suited to a wide range of secondary and tertiary alkyl amines using O2as the terminal oxidant have no precedent. This report describes a novel, green α-oxygenation of a wide range of linear and cyclic secondary and tertiary amines mediated by gold nanoparticles supported on alumina (Au/Al2O3). The observed catalysis was truly heterogeneous, and the catalyst could be reused. The present α-oxygenation utilizes O2as the terminal oxidant and water as the oxygen atom source of amides. The method generates water as the only theoretical by-product, which highlights the environmentally benign nature of the present reaction. Additionally, the present α-oxygenation provides a convenient method for the synthesis of18O-labeled amides using H218O as the oxygen source.

Asymmetric synthesis and evaluation of α-quaternary chiral lactam derivatives as novel anticancer agents

Asymmetric synthesis of α-quaternary chiral lactam derivatives as novel anticancer agents and evaluation of their cytotoxic potentials and spectrums are reported. Among the developed lactam derivatives, the most active new compounds (S)-4m and (S)-4n synthesized via asymmetric phase-transfer catalytic alkylation in very high optical yields (98 % ee) show promising in vitro anticancer activities with low micromolar IC50 values against colon, uterus, lung, and breast human cancer cells.

Amino-alcohol cyclization: Selective synthesis of lactams and cyclic amines from amino-alcohols

By employing an amination catalyst, previously used in the direct synthesis of amines from alcohol with ammonia, n-amino-alcohols could be selectively cyclized to either the amide or the amine. By the addition of water, the amine could be produced as the major product whereas adding a sacrificial ketone as a hydrogen acceptor resulted in the amide as the major product. Without an additive a mixture of both the amine and the amide was observed. N-substituted amino-alcohols solely gave cyclic amines under these conditions. From 2-(n-alkanol) anilines the cyclic amines were produced, where the n-propanol derivative selectively formed quinoline as the major product.

Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction

A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved version of the reaction are described.

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