477600-68-3

Usage

Uses

1. Used in Pharmaceutical Industry:
(3S,4S)-1-benzyl-N,4-dimethylpiperidin-3-amine hydrochloride is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs targeting specific medical conditions.
2. Used in Synthesis of Immunosuppressants:
In the pharmaceutical industry, (3S,4S)-1-benzyl-N,4-dimethylpiperidin-3-amine hydrochloride is used as a reagent in the preparation of piperidine derivatives that act as immunosuppressants. These immunosuppressants are crucial for the treatment of diseases associated with pathologic JAK3 activation, which can lead to various autoimmune disorders and transplant rejections.
3. Used in Research and Development:
Due to its unique chemical properties, (3S,4S)-1-benzyl-N,4-dimethylpiperidin-3-amine hydrochloride is also used in research and development for the creation of new compounds with potential therapeutic applications. Its versatility in chemical reactions makes it a valuable tool for scientists working on drug discovery and development.
4. Used in Chemical Synthesis:
(3S,4S)-1-benzyl-N,4-dimethylpiperidin-3-amine hydrochloride can be utilized as a building block in the synthesis of various organic compounds, including those with potential applications in materials science, agrochemicals, and other specialty chemicals.

InChI:InChI:1S/C14H22N2.2ClH/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;2*1H

Upstream product

• 1354621-59-2 cis-(1-benzyl-4-methyl-piperidin-3-yl)-methyl-amine 
• 1206824-89-6 tert-butyl methyl(4-methylpiperidin-3-yl)carbamate 
• 3430-22-6 3-Bromo-4-methylpyridin 
• 77862-24-9 4-Methyl-3-(methylamino)pyridine 
• 477600-70-7 N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine 
• 923036-28-6 (1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-yl)carbamic acid methyl ester 
• 32018-56-7 1-benzyl-4-methyl-1 ,2,3,6-tetrahydropyridine 
• 32018-96-5 1-benzyl-4-methyl-piperidin-3-one 
• 1228879-37-5 C₁₄H₂₂N₂*ClH 
• 1354621-59-2 (3S,4S)-1-benzyl-N,4-dimethylpiperidin-3-amine 
• 3430-27-1 3-amino-4-methylpyridine 

Relevant academic research and scientific papers

Investigation of practical routes for the kilogram-scale production of cis-3-methylamino-4-methylpiperidines

Two routes for the synthesis of cis-N-protected-3-methylamino-4- methylpiperidine (3) were examined: a route hinging on the electrochemical oxidation of carbamate 1 to install a ketone at the 3 position of the piperidine followed by reductive animation (disconnection A), and a route involving the hydrogenation of an appropriately functionalized pyridine (disconnection B). While both routes to the desired compound were ultimately successful, the pyridine hydrogenation approach proved to be more amenable to kilogram-scale preparations due to the crystallinity and purity of intermediates in that route.

Preparation method of tofacitinib intermediate cis-1-benzyl-N, 4-dimethylpiperidine-3-amine dihydrochloride

The invention discloses a preparation method of a tofacitinib intermediate cis-1benzyl-N, 4-dimethyl piperidine-3-amine dihydrochloride. The synthetic method comprises the following steps: taking 3-bromo-4-methylpyridine as an initial raw material, performing substitution reaction with amine to obtain a compound III, and performing acetyl or tert-butyloxycarbonyl protection and catalytic hydrogenation on the compound III to obtain a piperidine compound V. The compound V and benzaldehyde are subjected to reductive amination or react with benzyl halide to obtain a compound VI. A protecting groupis removed from the compound VI, and a hydrochloride compound I. 2HCl is formed at the same time. The synthesis method is simple to operate, high in total yield, high in product purity, stable in quality and suitable for industrial production.

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.

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.

Tropsch process for cloth intermediate (3 R, 4 R) - N, 4 - dimethyl -1 - benzyl -3 - amino piperdine and its oxalate salt hydrate of new synthetic method

The invention relates to a supporting france for cloth intermediate (3 R, 4 R) - N, 4 - dimethyl - 1 - benzyl - 3 - amino piperdine and its oxalate salt hydrate of new synthetic method. In order to 3 - amino - 4 - methyl pyridine as the starting material, its amino with orthoformate [...] is generated by the reaction, after after simple concentration, for the metal borohydride reduction to obtain N - methyl derivatives; Boc protection after the, re-covering and into a quaternary ammonium salt, the metal borohydride reduction, then the Rh catalyst for selective hydrogenation, form an enriched (3 R, 4 R - rel -) configuration of compounds, hydrochloric acid/alcohol system deprotected and into salt splitting removing (3 R, 4 S - rel -) isomer to, the resulting (3 R, 4 R - rel -) configuration product for free after L - DTTA obtained through splitting 3 R, 4 R - configuration product; splitting the resulting salts are free after through, into the oxalate purification, to further remove the residual small amount of 3 S, 4 S - isomer so as to obtain a corresponding high-purity and high optical purity (3 R, 4 R) - N, 4 - dimethyl - 1 - benzyl - 3 - amino piperdine. The method of the invention more beneficial for safe, simple and convenient of industrialized scale preparation Tropsch process for cloth intermediate (3 R, 4 R) - N, 4 - dimethyl - 1 - benzyl - 3 - amino piperdine oxalic acid salt hydrate.

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.

PROCESS FOR PREPARING CHIRAL AMINES

The invention pertains to a process for the preparation of an amine having at least two chiral centers from a ketone having a chiral center at the a position and an amine comprising the steps of: (a) contacting a ketone having a chiral center at the a position and a primary amine thereby forming an imine; (b) contacting the imine with a reducing agent in the presence of an enantioselective catalyst to form an amine having at least two chiral centers, wherein step (a) and/or step (b) are conducted under racemization-enhancing conditions, wherein the racemization-enhancing conditions are achieved by addition of an acid and/or by addition of a salt of a primary amine and an acid, which salt is added in addition to or instead of the primary amine, and wherein the reducing agent is hydrogen.

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.

A synthetic cis - 1 - benzyl - 3 - methylamino - 4 - methyl - piperidine

The invention relates to a method for synthesizing cis-1-benzyl-3-methylamino-4-methyl-piperidine, in particular to a method for synthesizing cis-1-benzyl-3-methylamino-4-methyl-piperidine by taking 1-benzyl-3-methylamino-4-methyl-piperidine bromide as an

Preparation method of tofacitinib intermediate

The invention relates to a novel preparation method of a tofacitinib intermediate and in particular to a preparation method of the tofacitinib intermediate (3R,4R)-1-benzyl-N-4-dimethyl piperidine-3-amine dihydrochloride. The preparation method comprises the following steps of: by taking 1-benzyl-4-methyl-1,2,3,6-tetrahydropyridine as an initial raw material, oxidizing olefin to form a ketone II by means of a one-step process; forming imine III with amine; applying asymmetric reduction imine to form amine; removing a trans isomer by recrystallization to obtain a cis-form structure IV; and finally, applying chiral resolution to obtain a final product (3R,4R)-1-benzyl-N-4-dimethyl piperidine-3-amine dihydrochloride I. The preparation method is creative in process, the process steps are shortened, and the synthetic yield of an asymmetric compound is greatly increased, thereby laying a solid foundation for industrial production.