Abstract
As part of a series of work dealing with the syntheses of water-soluble compounds allied with papaverine, 1-benzyl-2-methyl-6-methoxy-1, 2, 3, 4-tetrahydroisoquinoline-7-ol (XI) was prepared. Phenylacetyl chloride and 3-methoxy-4-benzyloxyphenethylamine were derived to the amide (VI) by the usual method, cyclized to 3, 4-dihydroisoquinoline compound (VII), and led to the objective XI via the methiodide (IX) or 1, 2, 3, 4-tetrahydroisoquinoline compound (X). Methylation of XI afforded II whose identification was established by the synthesis of II in the following manner. Homoveratrylamine and diazo ketone (IV) were submitted to the Arndt-Eistert reaction to form the amide (V), which was cyclized by the usual method, derived to the methiodide (VIII), and submitted to reduction.
