41183-02-2

Basic information

• Product Name: (±)-O-benzyllaudanidine
• Synonyms: (±)-O-benzyllaudanidine
• CAS NO: 41183-02-2
• Molecular Weight: 433.547
• Mol File: 41183-02-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (±)-O-benzyllaudanidine(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-O-benzyllaudanidine(41183-02-2)
• EPA Substance Registry System: (±)-O-benzyllaudanidine(41183-02-2)

Safety Data

• Hazardous Substances Data: 41183-02-2(Hazardous Substances Data)

Upstream product

• 110674-57-2 1-(2-amino-5-benzyloxy-4-methoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-2-methylisoquinoline 

Downstream Products

• 85-64-3 laudanine 
• 27841-87-8 O-benzylpallidine 
• 27841-87-8 (+/-)-O-benzylisosalutaridine 
• 93033-95-5 Acetic acid 4-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-1-methoxy-6-oxo-cyclohexa-2,4-dienyl ester 

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.