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Synlett 1990; 1990(10): 617-618
DOI: 10.1055/s-1990-21187
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Tandem and Stepwise Reactions of ß-(3,4-Dialkoxyphenyl)ethylamine Bis(aminol) Ethers in Syntheses of N-Arylmethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines: A Synthesis of Sendaverine Methyl Ether

Mark S. Cooper* , Martyn J. Earle, Robin A. Fairhurst, Harry Heaney, George Papageorgiou, Robert F. Wilkins
  • *Department of Chemistry, Loughborough University of Technology, Leicestershire, LE11 3TU, England
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Publication Date:
08 March 2002 (online)

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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.