477600-70-7

Basic information

• Product Name: (3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine
• Synonyms: (3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine;(Cis)-Benzyl-N,4-diMethylpiperidin-3-aMine;(3R,4R)-1-benzyl-N,4-diMethylpiperidin-3-aMine hydrochloride;3-PiperidinaMine, N,4-diMethyl-1-(phenylMethyl)-, (3R,4R)-;(3R,4R)-(1-benzyl-4-Methylpiperidin-3-yl)MethylaMine;(3R,4R)-1-Benzyl-N,4-diMe...;(3R,4R)-1-Benzyl-N-Methyl-4-Methylpiperidin-3-aMine;(3R,4R)-1-BENYL-N,4-DIMETHYLPIPERIDIN-3-AMINE
• CAS NO: 477600-70-7
• Molecular Formula: C₁₄H₂₂N₂
• Molecular Weight: 218.33788
• Mol File: 477600-70-7.mol
• Article Data: 11

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.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.26±0.40(Predicted)
• CAS DataBase Reference: (3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine(477600-70-7)
• EPA Substance Registry System: (3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine(477600-70-7)

Safety Data

• Hazardous Substances Data: 477600-70-7(Hazardous Substances Data)

Usage

Description

(3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine, also known as D464895, is an organic compound with a specific stereochemistry characterized by its 3R and 4R configurations. It is a reagent used in the synthesis of various pharmaceutical compounds, particularly those targeting Janus tyrosine kinases.

Uses

Used in Pharmaceutical Industry:
(3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine is used as a reagent for the preparation of Janus tyrosine kinase inhibitors. These inhibitors are crucial in the treatment of autoimmune diseases, as they help regulate the immune system and prevent it from attacking the body's own cells.
Used in Autoimmune Disease Treatment:
(3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine is used as a key component in the development of drugs that target Janus tyrosine kinases. By inhibiting these enzymes, the compound can help manage and treat various autoimmune diseases, such as rheumatoid arthritis, psoriasis, and inflammatory bowel disease, among others. (3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine's role in the development of these drugs is to provide a structural framework that can be further modified and optimized for therapeutic use.

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+/m1/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

• 923036-30-0 N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-(7-p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1062580-52-2 N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride 
• 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

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.

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.