Tandem and Stepwise Reactions of β-(3,4-Dialkoxyphenyl)ethylamine Bis(aminol) Ethers in Syntheses ofN-Arylmethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines: A Synthesis of Sendaverine Methyl Ether
- 1 January 1990
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (10) , 617-618
- https://doi.org/10.1055/s-1990-21187
Abstract
The bis(aminol) ether 1 [N,N-bis(methoxymethyl)-2-(3,4-dimethoxyphenyl)ethylamine] gives with trichloromethyl-silane 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 affords good yields of N-arylmethyl derivatives. A short synthesis of sendaverine methyl ether (6,7-dimethoxy-2-(4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline) is reported.Keywords
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