47653-40-7

Basic information

• Product Name: (±)-O-benzylarmepavine
• Synonyms: (±)-O-benzylarmepavine
• CAS NO: 47653-40-7
• Molecular Weight: 403.521
• Mol File: 47653-40-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (±)-O-benzylarmepavine(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-O-benzylarmepavine(47653-40-7)
• EPA Substance Registry System: (±)-O-benzylarmepavine(47653-40-7)

Safety Data

• Hazardous Substances Data: 47653-40-7(Hazardous Substances Data)

Upstream product

• 115385-69-8 1-(4-benzyloxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinolinium chloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 14301-36-1 N-[2-(3,4-dimethoxyphenyl)ethyl]formamide 
• 51714-24-0 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 30045-07-9 2-methyl-6,7-dimethoxy-3,4-dihydroisoquinolinium iodide 

Downstream Products

• 5884-67-3 armepavine 

Relevant articles and documents

Synthesis of alkaloids by stevens rearrangement of nitrile-stabilized ammonium ylides: (±)-laudanosine, (±)-laudanidine, (±)-armepavine, (±)-7-methoxycryptopleurine, and (±)-xylopinine

The Stevens rearrangement of nitrile-stabilized ammonium ylides in conjunction with the reductive removal of the nitrile function permits the facile construction of α-branched amines from α-aminonitriles. We employed this reaction sequence for the preparation of (±)-laudanosine, (±)-laudanidine and (±)-armepavine, (±)-7- methoxycryptopleurine, and (±)-xylopinine from two closely related and readily accessible bicyclic α-aminonitriles. The final products were obtained in high to almost quantitative yields (71-98%) from the quaternary ammonium salts obtained by N-alkylation of these starting materials.