32018-96-5

Basic information

• Product Name: 1-benzyl-4-methylpiperidin-3-one
• Synonyms: 1-benzyl-4-methylpiperidin-3-one;4-Methyl-1-(phenylmethyl)-3-piperidinone;3-Piperidinone, 4-Methyl-1-(phenylMethyl)-;Methyl-1-(phenylMethyl) 3-piperidone hydrochloride;1-benzyl-4-methylpiperidin-3-on
• CAS NO: 32018-96-5
• Molecular Formula: C₁₃H₁₇NO
• Molecular Weight: 203.28
• EINECS: 1312995-182-4
• Mol File: 32018-96-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 302.9°C at 760 mmHg
• Flash Point: 128.085°C
• Appearance: /
• Density: 1.057
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 6.13±0.40(Predicted)
• CAS DataBase Reference: 1-benzyl-4-methylpiperidin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-4-methylpiperidin-3-one(32018-96-5)
• EPA Substance Registry System: 1-benzyl-4-methylpiperidin-3-one(32018-96-5)

Safety Data

• Hazardous Substances Data: 32018-96-5(Hazardous Substances Data)

Usage

Synthesis

A 640-L vessel was charged with SO3.pyridine (51.47 kg, 323.1 mol). DMSO (169 L) was added and the whole was heated slowly to 33 °C. After a solution was obtained, it was cooled to 25 °C. The TsOH salt of the amine (40.9 kg, 107.7 mol) was added into the vessel and suspended in DMSO (50 L). After the addition of Et3N (62 L, 43.8 mol), the SO3.pyridine solution in DMSO was added to the two-phase mixture in the vessel at such a rate as to keep the internal temperature below 25 °C. After 1 h of stirring at 22 °C, the reaction was 92% complete. The mixture was cooled to 10 °C and quenched with water (182 L) over a period of 40 min at such a rate as to keep the internal temperature below 17 °C; a 25% NH3 solution (16 L) was then added. After phase separation, the aqueous phase was extracted with three portions of toluene (3 × 60 L) while controlling the pH of the aqueous layer to 10 after each extraction. The combined organic phases (approximately 240 L) were extracted with water ?(61 L), and the bright-orange solution was heated at 40?50 °C jacket temperature over 1 h while blowing a nitrogen stream into the solution via an immersing tube. Then, toluene (170 L) was stripped off at 50 °C to afford the ketone (50.84 kg, 93%) as an orange solution in toluene.

Uses

1-Benzyl-4-methylpiperidin-3-one is an intermediate used to prepare pyrrolo[2,3-d]pyrimidine compds. as inhibitors of protein kinases.

InChI:InChI=1/C13H17NO/c1-11-7-8-14(10-13(11)15)9-12-5-3-2-4-6-12/h2-6,11H,7-10H2,1H3

Upstream product

• 55181-09-4 1-benzyl-4-methyl-2,6-dihydropiperidine-3-one 
• 142918-38-5 3-methoxy-4-methylpyridine 
• 3430-22-6 3-Bromo-4-methylpyridin 
• 14773-55-8 3-ethoxy-4-methylpyridine 
• 1679-47-6 3-methyltetrahydro-2-furanone 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 1408076-42-5 4-methylpiperidin-3-one hydrochloride 
• 384338-20-9 1-benzyl-4-methylpiperidin-3-ol 
• 175406-94-7 1-benzyl-3-oxopiperidine-4-carboxylic acid methyl ester 
• 3430-27-1 3-amino-4-methylpyridine 
• 1121-19-3 4-methylpyridin-3-ol 

Downstream Products

• 384338-23-2 (1-benzyl-4-methyl-piperidin-3-yl)-methyl-amine 
• 374794-77-1 tert-butyl 4-methyl-3-oxopiperidine-1-carboxylate 
• 1312762-44-9 (3R,4R)-3-methylamino-4-methylpiperidine-1-carboxylic acid tert-butyl ester 
• 1312762-43-8 (3R,4R)-4-methyl-3-(methyl-((R)-1-phenylethyl)amino)piperidine-1-carboxylic acid tert-butyl ester 
• 1062580-52-2 N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride 
• 477600-74-1 tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate 
• 1228879-37-5 cis-N-benzyl-3-methoxycarbonylamino-4-methylpiperidine bis(hydrochloride) 
• 477600-70-7 N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine 
• 1354621-59-2 (3S,4S)-1-benzyl-N,4-dimethylpiperidin-3-amine 
• 1228879-37-5 (3R,4R)-1-benzyl-N,4-dimethylpiperidine-3-amine dihydrochloride 
• 384338-20-9 1-benzyl-4-methylpiperidin-3-ol 
• 1354621-59-2 C₁₄H₂₂N₂ 
• 1228879-37-5 C₁₄H₂₂N₂*ClH 
• 1207853-61-9 (3R,4R)-3-amino-4-methylpiperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Synthesis and application of 1-benzyl-4-methyl-5-alkoxy-1, 2, 3, 6-tetrahydropyridine derivative

The invention relates to the field of synthesis of drug intermediates, in particular to the field of synthesis of key intermediates for preparing anti-rheumatoid arthritis drug tofacitinib, and specifically relates to a 1-benzyl-4-methyl-5-alkoxy-1, 2, 3, 6-tetrahydropyridine compound, a synthetic method thereof, and an application of the 1-benzyl-4-methyl-5-alkoxy 1, 2, 3, 6-tetrahydropyridine compound in preparation of a key intermediate cis-1-benzyl-3-methylamino-4-methyl piperidine of tofacitinib.

4-methylpiperidine-3-ketone and simple preparation method of 4-methylpiperidine-3-ketone derivative

The invention relates to 4-methylpiperidine-3-ketone and a simple preparation method of a 4-methylpiperidine-3-ketone derivative. According to the 4-methylpiperidine-3-ketone and the simple preparation method of the 4-methylpiperidine-3-ketone derivative, 1-nitro-3-methyl-5-hydroxy n-amyl-2-ketone is prepared by using a reaction of alpha-methyl-gamma-butyrolactone and nitromethane, then 1-nitro-3-methyl-5-protection oxy-n-pentyl-2-ketone is obtained through sulfonyl chloride reagent protection hydroxide radical, then nitro is reduced to amino through hydrogenation, and meanwhile 4-methylpiperidine-3-ketone is obtained through cyclization. The invention further provides a method for preparing 2-chlorin-3-amino-4-methylpyridine and N-benzyl-4-methylpiperidine-3-ketone from 4-methylpiperidine-3-ketone. Raw materials used in the simple preparation method and the method are cheap and readily available, the condition is mild, operation is simple and convenient and safe, reaction selectivityis high, the product yield and purity are high, the cost is low, the amount of "three wastes" is low, and environmental protection is realized.

Synthesis method of tofacitinib intermediate (3R, 4R)-1-benzyl-N,4-dimethylpiperidine-3-amine

The invention discloses a synthesis method of a tofacitinib intermediate (3R, 4R)-1-benzyl-N,4-dimethylpiperidine-3-amine. The synthesis method comprises the steps: making 3-chlorobutyraldehyde (II) serving as a raw material react with sodium cyanide, then, carrying out Leuckart-Wallach reaction and a Thorpe-Ziegler reaction, next, reacting with a 30% methylamine methanol solution to generate enamine, and carrying out asymmetric catalytic hydrogenation to obtain a final product (3R, 4R)-1-benzyl-N,4-dimethylpiperidine-3-amine (I). In the synthesis method, a compound VI is synthesized by a Thorpe-Ziegler reaction, and the yield is high; and due to the adoption of the asymmetric catalytic hydrogenation, the final product is not needed to be subjected to chiral resolution, the total yield andpurity are high, and few byproducts are generated.