50373-11-0

Basic information

• Product Name: 3-Piperidinemethanol, 1-methyl-4-phenyl-, cis-
• CAS NO: 50373-11-0
• Molecular Formula: C13H19NO
• Molecular Weight: 205.3
• Mol File: 50373-11-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-Piperidinemethanol, 1-methyl-4-phenyl-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Piperidinemethanol, 1-methyl-4-phenyl-, cis-(50373-11-0)
• EPA Substance Registry System: 3-Piperidinemethanol, 1-methyl-4-phenyl-, cis-(50373-11-0)

Safety Data

• Hazardous Substances Data: 50373-11-0(Hazardous Substances Data)

Upstream product

• 86219-77-4 3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine 
• 116140-25-1 (+/-)-6-oxo-4t-phenyl-piperidine-3r-carboxylic acid ethyl ester 
• 626-67-5 N-methylcyclohexylamine 

Relevant articles and documents

Transition-Metal-Free Multiple Functionalization of Piperidines to 4-Substituted and 3,4-Disubstituted 2-Piperidinones

Remote and multiple functionalization of piperidines without the use of transition-metal catalysts and elaborate directing groups is one of the major challenges in organic synthesis. Herein is reported an unprecedented two-step protocol that enables the multiple functionalization of piperidines to either 4-substituted or trans-3,4-disubstituted 2-piperidones. First, by exploiting the duality of TEMPO reactivity, which under oxidative and thermal conditions fluctuates between cationic and persistent-radical form, a novel multiple C(sp3)-H oxidation of piperidines to α,β-unsaturated 2-piperidones was developed. Second, the intrinsic low reactivity of the unsaturated piperidones toward conjugated Grignard additions was overcome by using trimethylsilyl chloride (TMSCl) as Lewis acid. Subsequently, conjugated Grignard addition/electrophilic trapping protocol provided substituted 2-piperidone intermediates, some of which were then transformed into pharmaceutical alkaloids.