1062580-52-2 Usage
Description
CIS-N-BENZYL-3-METHYLAMINO-4-METHYL-PIPERIDINE BIS-(HYDROCHLORIDE) is a chemical compound with the molecular formula C16H24N2·2HCl. It is a derivative of piperidine, an organic compound that is a heterocyclic amine. CIS-N-BENZYL-3-METHYLAMINO-4-METHYL-PIPERIDINE BIS-(HYDROCHLORIDE) is characterized by its benzyl and methylamino groups, which contribute to its chemical properties and potential applications.
Uses
Used in Pharmaceutical Industry:
CIS-N-BENZYL-3-METHYLAMINO-4-METHYL-PIPERIDINE BIS-(HYDROCHLORIDE) is used as a pharmaceutical intermediate for the development of various drugs. Its structural features make it a valuable building block in the synthesis of complex molecules with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic chemistry, CIS-N-BENZYL-3-METHYLAMINO-4-METHYL-PIPERIDINE BIS-(HYDROCHLORIDE) serves as an intermediate in the synthesis of more complex organic compounds. Its unique functional groups can be further modified or reacted to create a wide range of chemical products.
Used in Research and Development:
CIS-N-BENZYL-3-METHYLAMINO-4-METHYL-PIPERIDINE BIS-(HYDROCHLORIDE) is also utilized in laboratory research and development processes. It can be employed to study the effects of its structural features on various chemical and biological properties, potentially leading to the discovery of new drugs or materials.
Used in the Preparation of Janus Kinase Inhibitors:
CIS-N-BENZYL-3-METHYLAMINO-4-METHYL-PIPERIDINE BIS-(HYDROCHLORIDE) is related to the compound (3R,4R)-N,4-Dimethyl-1-(phenylmethyl)-3-piperidinamine Hydrochloride, which is used to prepare Janus kinase 1 (JAK1) selective inhibitors. These inhibitors are important in the treatment of various diseases, including autoimmune disorders and cancer, by targeting the JAK/STAT signaling pathway.
Synthesis
The TiCl4(0.2g, 1mmol), NEt3(0.15g, 1 . 5mmol) suspended 200 ml in toluene, then add 1-benzyl-4-methyl-3-ketone piperidine (20.3g, 100mmol), temperature control 35 °C methylamine solution is added to the reaction solution (9.32g, 120mmol) reaction 4 hours, adding NaBH (OAC) 3 (0.32g, 1 . 5mmol), glacial acetic acid 2 ml, temperature control 35 °C reaction, thin layer monitoring after the reaction is complete. Adding saturated salt water washing, anhydrous sodium sulfate for drying the organic phase, the organic phase concentrated, with residues 35% hydrochloric acid ethanol re-crystallization, to obtain (3R, 4R)-cis-1-benzyl-4-methyl-3-methylamino-piperidine dihydrochloride 17.2g, yield 85.0%, optical purity 99.0% (HPLC method).
Check Digit Verification of cas no
The CAS Registry Mumber 1062580-52-2 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,6,2,5,8 and 0 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1062580-52:
(9*1)+(8*0)+(7*6)+(6*2)+(5*5)+(4*8)+(3*0)+(2*5)+(1*2)=132
132 % 10 = 2
So 1062580-52-2 is a valid CAS Registry Number.
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
1062580-52-2Relevant articles and documents
Asymmetric Synthesis of a Key Intermediate for Tofacitinib via a Dynamic Kinetic Resolution-Reductive Amination Protocol
Verzijl, Gerard K. M.,Schuster, Christian,Dax, Thomas,De Vries, André H. M.,Lefort, Laurent
, p. 1817 - 1822 (2018)
We report the first example of a catalytic asymmetric reductive amination under dynamic kinetic resolution (DKR) conditions for the preparation of a chiral amine as a key intermediate toward Tofacitinib, an active pharmaceutical ingredient developed by Pfizer. Such a protocol allows the preferential formation of a single product out of four possible diastereomers of the chiral amine starting from the corresponding racemic ketone. The chiral iridium catalyst able to perform such a feast was discovered through a mix of high-throughput screening, racemization study, and reaction optimization.
PROCESS FOR THE PREPARATION OF CHIRAL 3-AMINO-PIPERIDINS, USEFUL INTERMEDIATES FOR THE PREPARATION OF TOFACITINIB
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, (2019/01/15)
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.
Preparation method for chiral piperylhydrazine compound and recycling method for chiral resolving agent
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Paragraph 0012; 0015; 0017; 0020; 0022; 0025, (2019/01/08)
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.