477600-69-4

Basic information

• Product Name: (3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine
• Synonyms: (3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine;(3R,4R)-rel-N,4-Dimethyl-1-(phenylmethyl)-3-Piperidinamine;(3S,4S)-1-benzyl-N,4-diMethylpiperidin-3-aMine (rel);3-PiperidinaMine, N,4-diMethyl-1-(phenylMethyl)-, (3R,4R)-rel-;3-piperidinaMine, N,4-diMethyl-1-(phenylMethyl)-, (3S,4S)-;cis-1-Benzyl-N,4-diMethylpiperidin-3-aMine;(3S,4S)-(1-Benzyl-4-methyl-piperidin-3-yl)-methyl-amine;Tofacitinib Impurity 26
• CAS NO: 477600-69-4
• Molecular Formula: C14H22N2
• Molecular Weight: 218.33788
• EINECS: 1312995-182-4
• Mol File: 477600-69-4.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 302.6°Cat760mmHg
• Flash Point: 107.4°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 0.000978mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 10.26±0.40(Predicted)
• CAS DataBase Reference: (3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine(477600-69-4)
• EPA Substance Registry System: (3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine(477600-69-4)

Safety Data

• Hazardous Substances Data: 477600-69-4(Hazardous Substances Data)

Usage

Uses

(3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine is a reagent used in the preparation of substituted pyrrrolipyrimidinamines as Januus kinase inhibitors (CP-352,664), for the treatment of autoimmune diseases and organ transplant rejection.

InChI:InChI=1/C14H22N2/c1-12-8-9-16(11-14(12)15-2)10-13-6-4-3-5-7-13/h3-7,12,14-15H,8-11H2,1-2H3/t12-,14+/m0/s1

Upstream product

• 923036-28-6 (1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-yl)carbamic acid methyl ester 
• 923036-27-5 1-benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromide 
• 1092578-34-1 tert-butyl (3R,4R)-1-benzyl-4-methylpiperidin-3-ylcarbamate 
• 100-46-9 benzylamine 
• 74-89-5 methylamine 
• 32018-96-5 1-benzyl-4-methyl-piperidin-3-one 
• 6998-30-7 methylamine acetate 
• 1615709-89-1 1-benzyl-4-methyl-3-(methylamino)pyridinium bromide 
• 3430-27-1 3-amino-4-methylpyridine 
• 1062580-52-2 N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride 
• 384338-20-9 1-benzyl-4-methylpiperidin-3-ol 
• 384338-23-2 (1-benzyl-4-methyl-piperidin-3-yl)-methyl-amine 
• 77303-35-6 4-methyl-2,6-dioxo-1,2,5,6-tetrahydro-pyridine-3-carbonitrile 

Downstream Products

• 1616761-00-2 3-[(3R,4R)-3-({2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl}(methyl)amino)-4-methylpiperidin-1-yl]-3-oxopropanenitrile 

Relevant articles and documents

Synthesis method of tofacitinib citrate diastereomer impurities

The invention discloses a synthesis method of tofacitinib citrate diastereomer impurities, relates to the technical field of drug organic synthesis, and relates to 3 - amino -4 - methylpyridine as a starting material and a quaternary ammonium salt. Raw materials of the whole synthetic route are easily available, the reaction conditions are mild, the post-treatment separation and purification operation is simple and feasible, and the preparation method is good in repeatability.

Preparation methods of tofacitinib intermediate amine and dihydrochloride thereof

The invention discloses preparation methods of tofacitinib intermediate amine and dihydrochloride thereof. According to the preparation method of the tofacitinib intermediate amine, methyl acetoacetate and cyanoacetamide are taken as starting materials and subjected to condensation, olefinic bond reduction, cyano hydrolysis into amide, N benzylation and Hofmann degradation to prepare primary amine, monomethylation and chiral resolution of the primary amine are performed, and a carbonyl group is reduced with zinc borohydride, so a target product is obtained. The obtained (3R,4R)-1-benzyl-3-methylamino-4-methylpiperidine is subjected to salifying with hydrochloric acid to obtain the dihydrochloride. The methods have the advantages that the whole process avoids a high-pressure hydrogenation reaction under an acidic condition; all the reaction steps adopt conventional reaction reagents and solvents, so raw material sources are not limited, and cost is low; and the method avoids a lithium aluminum hydride reduction reagent with high risk, each step has high selectivity, the reaction product of each step can be easily refined, and the method has advantages in industrialization.

PROCESS FOR THE PREPARATION OF CHIRAL 3-AMINO-PIPERIDINS, USEFUL INTERMEDIATES FOR THE PREPARATION OF TOFACITINIB

Object of the present invention is an improved process for the preparation of (3R,4R)-1-benzyl-4-methylpiperidin-3-amine by means of chiral Rhodium catalysts.