The Synthesis of 2-Arylmethyltetrahydroisoquinolines from Bis(Aminol) Ethers Involving Two Iminium Salt Intermediates

Article abstract of DOI:10.1016/0040-4020(95)00639-P

The bis(aminol) ether derived from 3,4-dimethoxy-β-phenylethylamine, methanol, and formaldehyde reacts with trichloromethylsilane to afford an equilibrium mixture of N-chloromethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline and its related iminium chloride.Interaction with electron rich aromatic compounds afford good yields of N-arylmethyl derivatives, including sendaverine methyl ether.Reactions of the bis(amino) ether in the presence of the aromatic substrate allows the formation of the N-arylmethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives in a one pot reaction.