7006-50-0

Basic information

• Product Name: (1-Benzyl-piperidin-4-yl)-methyl-amine
• Synonyms: 1-Benzyl-N-methylpiperidin-4-amine;4-(Methylamino)-1-benzylpiperidine;(1-BENZYL-PIPERIDIN-4-YL)-N-METHYL-AMINE;1-Benzyl-N-methyl-4-piperidinamine;1-Benzyl-4-(methylamino)piperidine;1-Benzyl-4-(N-methyl)piperidinamine;1-Benzyl-4-(methylamino)piperidin
• CAS NO: 7006-50-0
• Molecular Formula: C₁₃H₂₀N₂
• Molecular Weight: 204.31
• Product Categories: Amines and Anilines;Heterocycles;Piperidine
• Mol File: 7006-50-0.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 110°/0.7mm
• Flash Point: 126.4 ºC
• Appearance: /
• Density: 1.018 g/cm³
• Vapor Pressure: 0.00184mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.30±0.20(Predicted)
• CAS DataBase Reference: (1-Benzyl-piperidin-4-yl)-methyl-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Benzyl-piperidin-4-yl)-methyl-amine(7006-50-0)
• EPA Substance Registry System: (1-Benzyl-piperidin-4-yl)-methyl-amine(7006-50-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 7006-50-0(Hazardous Substances Data)

Usage

Uses

1-Benzyl-N-methylpiperidin-4-amine is a useful intermediate used in the synthesis of Taladegib; a small molecular hedgehog signaling pathway inhibitor.

InChI:InChI=1/C13H20N2/c1-14-13-7-9-15(10-8-13)11-12-5-3-2-4-6-12/h2-6,13-14H,7-11H2,1H3

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 593-51-1 methylamine hydrochloride 
• 478832-19-8 N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoro-N-methylacetamide 
• 7144-05-0 4-Aminomethylpiperidine 
• 100-44-7 benzyl chloride 
• 144-55-8 sodium hydrogencarbonate 
• 7732-18-5 water 
• 64951-37-7 ethyl (1-phenylmethyl-4-piperidyl)carbamate 
• 100-39-0 benzyl bromide 
• 73874-95-0 tert-butyl N-(piperidin-4-yl)carbamate hydrochloride 
• 620-08-6 4-methoxypyridine 
• 100-59-4 phenylmagnesium chloride 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 50541-93-0 4-amino-1-benzylpiperidine 

Downstream Products

• 170856-57-2 N-(1-benzylpiperidin-4-yl)-N-(3-ethoxypyridin-2-yl)-methylamine 
• 179556-82-2 (1-benzyl-piperidin-4-yl)-(3-isopropoxy-pyridin-2-yl)-methyl-amine 
• 179556-59-3 1-benzyl-4-(N-methyl-N-(3-cyano-2-pyridinyl)amino)piperidine 
• 179556-50-4 1-benzyl-4-(N-methyl-N-(3-methoxycarbonyl-2-pyridinyl)amino)piperidine 
• 179556-25-3 1-benzyl-4-(N-methyl-N-(3-formyl-2-pyridinyl)amino)piperidine 
• 34737-89-8 1-Benzyl-3-methyl-4-piperidon 
• 139679-51-9 N-Butyl-N'-[1-(phenylmethyl)-4-piperidinyl]urea 
• 1259510-81-0 C₂₆H₃₁N₅O₂S 
• 1365156-90-6 tert-butyl methyl(1-(6-methylpyrazin-2-yl)piperidin-4-yl)carbamate 
• 1258861-20-9 4-fluoro-N-methyl-N-{1-[4-(1-methyl-1H-pyrazole-5-yl)phthalazin-1-yl]piperidin-4-yl}-2-(trifluoromethyl)benzamide 
• 405058-03-9 1-(3'-pyridyl)-4-(N-Boc-N-methyl)aminopiperidine 

Relevant articles and documents

Nitrogen heterocyclic compound, pharmaceutical composition containing nitrogen heterocyclic compound, and preparation method and application of nitrogen heterocyclic compound

Disclosed are a nitrogen heterocyclic compound represented by a formula (I), a pharmaceutical composition comprising the same, and a preparation method and use of the nitrogen heterocyclic compound, and in particular, relates to the use of the nitrogen heterocyclic compound for prevention or treatment of diseases or conditions associated with RET activity.

Design, synthesis and evaluation of (R)-3-(7-(methyl?7H-pyrrolo?2, 3-d]pyrimidin-4-yl)amino)-5-azaspiro?2.4]heptan-5-yl)-3-oxopropanenitrile as a JAK1-selective inhibitor

Based on (R)-N-methyl-N-(5-azaspiro?2.4]heptan-7-yl)-7H-pyrrolo?2, 3-d]pyrimidin-4-amine as a core scaffold, we identified (R)-3-(7-(methyl?7H-pyrrolo?2, 3-d]pyrimidin-4-yl)amino)-5-azaspiro?2.4]heptan-5- yl)-3-oxopropanenitrile [(R)-6c] as a JAK1 selective inhibitor. The structural design was based on the combination of tofacitinib's 7-deazapurine and 5-azaspiro?2.4]heptan-7-amine. Compound (R)-6c exhibited an IC50 value of 8.5 nM against JAK1 with a selectivity index of 48 over JAK2. To optimize (R)-6c as a lead compound, we performed in vitro ADME, hERG, kinase profiling, and pharmacokinetic tests. Mouse and rat in vivo studies verified that (R)-6c exhibited desired efficacies in CIA and AIA models.

Synthetic method of Taladegib

The invention discloses a synthetic method of Taladegib. The synthetic method is characterized by comprising the following steps that reductive amination is carried out on N-benzyl-4-piperidone to obtain a compound in formula VI; in the presence of an organic base, an acylation reaction is carried out on the compound in the formula VI and an acylation reagent to obtain a compound in the formula VIII; the acylation reagent is 4-fluoro-2-(trifluoromethyl)benzoyl chloride; in the presence of a hydrogen source and a palladium catalyst, debenzylation is carried out on the compound in formula VIII to obtain a compound in the formula IX; in the presence of an inorganic base, the compound in the formula IX is reacted with 1,4-dichloro phthalazine to obtain a compound in the formula X; in the presence of the inorganic base and the palladium catalyst, an SUZUKI coupling reaction is carried out on the compound in the formula X and 1-methyl-1H-pyrazole-5-boronic acid pinacol ester to obtain Taladegib. According to the invention, the process route is improved, cheap N-benzyl-4-piperidone is taken as a starting material, the processes of Boc protection and deprotection are removed to reduce the synthesis steps and reduce the production cost.