384338-23-2

Basic information

• Product Name: 1-BENZYL-N,4-DIMETHYLPIPERIDIN-3-AMINE DIHYDROCHLORIDE
• Synonyms: (1-Benzyl-4-Methylpiperidin-3-yl)MethylaMine or dihydrochloride;raceMic Mixture tofacitinib interMediat;Tofacitinib IMpurity F;N,4-dimethyl-1-(phenylmethyl)-3-Piperidinamine;1-BENZYL-N,4-DIMETHYLPIPERIDIN-3-AMINE DIHYDROCHLORIDE;3-PiperidinaMine, N,4-diMethyl-1-(phenylMethyl)-;(1-Benzyl-4-methylpiperidin-3-yl)methylamine;1-Benzyl-N-methyl-4-methylpiperidin-3-amine
• CAS NO: 384338-23-2
• Molecular Formula: C₁₄H₂₂N₂
• Molecular Weight: 291.25976
• Mol File: 384338-23-2.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-BENZYL-N,4-DIMETHYLPIPERIDIN-3-AMINE DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL-N,4-DIMETHYLPIPERIDIN-3-AMINE DIHYDROCHLORIDE(384338-23-2)
• EPA Substance Registry System: 1-BENZYL-N,4-DIMETHYLPIPERIDIN-3-AMINE DIHYDROCHLORIDE(384338-23-2)

Safety Data

• Hazardous Substances Data: 384338-23-2(Hazardous Substances Data)

Usage

Uses

N,4-Dimethyl-1-benzyl-3-piperidinamine is an impurity of Tofaritinib (C781351) a pyrrolo[2,3-d]pyrimidine derivative, as Janus kinase inhibitor for treatment of rheumatoid arthritis.

Upstream product

• 100-44-7 benzyl chloride 
• 74-89-5 methylamine 
• 384338-20-9 1-benzyl-4-methylpiperidin-3-ol 
• 3430-27-1 3-amino-4-methylpyridine 
• 32018-96-5 1-benzyl-4-methyl-piperidin-3-one 
• 593-51-1 methylamine hydrochloride 
• 1615709-89-1 1-benzyl-4-methyl-3-(methylamino)pyridinium bromide 
• 3430-22-6 3-Bromo-4-methylpyridin 
• 108-89-4 picoline 
• 107-31-3 Methyl formate 
• 1039738-27-6 1-benzyl-4-methyl-3-amino piperidine 
• 1548270-19-4 1-benzyl-4-methyl-3-(methylamino)piperidin-4-ol 
• 1548270-41-2 C₁₄H₂₀N₂ 
• 1548270-43-4 C₁₄H₂₀N₂ 

Downstream Products

• 1252883-87-6 N-(1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1062580-52-2 N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride 
• 1228879-37-5 (3R,4R)-1-benzyl-N,4-dimethylpiperidine-3-amine dihydrochloride 
• 477600-70-7 N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine 
• 540737-29-9 Tofacitinib citrate 
• 1259404-17-5 tasocitinib 
• 384336-73-6 (3R,4R)-methyl-(4-methyl-piperidin-3-yl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine 
• 384337-90-0 methyl(1-phenylmethyl-4-methylpiperidin-3-yl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine 

Relevant articles and documents

Preparation methods of tofacitinib citrate intermediate and tofacitinib citrate

The invention discloses preparation methods of a tofacitinib citrate intermediate and tofacitinib citrate. The preparation method of the tofacitinib citrate intermediate comprises: preparing N-(1-benzyl-4-methyl-1,2,5,6-tetrahydropiperidine-3-yl)acetamide by using 3-amino-4-methyl-pyridine, acetyl chloride, benzyl chloride and sodium borohydride as raw materials; preparing 1-benzyl-N,4-dimethylpiperidine-3-amine by using the N-(1-benzyl-4-methyl-1,2,5,6-tetrahydropiperidine-3-yl)acetamide, hydrochloric acid, methylamine and sodium borohydride as raw materials; and carrying out resolution and dissociation on the 1-benzyl-N,4-dimethylpiperidine-3-amine, and carrying out salt forming with hydrochloric acid to obtain the product. The invention provides the new tofacitinib citrate intermediatepreparation method, wherein the use amount of the catalytic hydrogenation catalyst is reduced in the preparation process of tofacitinib citrate so as to reduce the cost, and the generation of N-alkylated impurities can be well controlled by adopting the isopropanol/water mixed solvent.

Preparation method for chiral piperylhydrazine compound and recycling method for chiral resolving agent

The invention discloses a preparation method for a chiral piperylhydrazine compound and a recycling method for a chiral resolving agent. In the invention, 1-benzyl-4-methyl-3-pipradrol is taken as aninitial raw material and is subjected to reactions of halogenation, methylamination, chiral resolution, and the like, so as to prepare a (3R, 4R)-N,4-dimethyl-1-(phenyl methyl)-3-piperylhydrazine dihydrochloride product, and meanwhile, a resolving mother solution is subjected to alkalization, refined, purified and recycled, so as to acquire a (2R,3R)-2,3-bi[(4-methyl benzoyl) oxo] succinic acid product meeting the reaction requirement. The invention has the beneficial effects of 1) short synthetic route, easily controlled intermediate purity and benefit to the control on impurity content, and2) simple and convenient technological operation in each step reaction, capability of recycling the high-dosage chiral resolving agent, capability of reducing production cost while reducing yield of solid wastes and suitability for large-scale industrial production.

AN IMPROVED PROCESS FOR THE PREPARATION OF (3R,4R)-(1-BENZYL-4-METHYLPIPERIDIN-3-YL)-METHYLAMINE

The present invention is related to an improved and efficient process for preparation of (3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine which comprises: (a) N-acylation of 3-Amino-4-methyl pyridine; (b) Quarternization of 3-Acetylamino-4- methyl pyridine using benzyl halide; (c) Partial reduction of quarternized 3-Acetylamino- 4-methyl pyridine by Sodium borohydride in Methanol or water; (d) Hydrolysis of partially reduced product to 1-Benzyl-4-methylpiperidin-3-one in presence of acid; (e) Reductive animation of 1-Benzyl-4-methylpiperidin-3-one using Methanolic methylamine in presence of Titanium(IV) isopropoxide in Methanol; (f) Resolution of 1-Benzyl-4- methylpiperidin-3-yl)-methylamine using Ditoluoyl (L) tartaric acid to get (3R,4R)-(1- benzyl-4-methylpiperidin-3-yl)-methylamine. The invention is also related to novel intermediates.