1967 Volume 87 Issue 7 Pages 757-760
Fusion-condensation of 4-benzyloxy-3-methoxyphenethylamine (III) and 4-hydroxyphenyl-acetic acid (IV) gives the amide (V) and its mesylation with methanesulfonyl chloride in pyridine afforded N-(4-benzyloxy-3-methoxyphenethyl)-2-(p-methylsulfonyloxyphenyl) acetamide (VI), which agreed in its properties with the amide compound reported in the preceding paper. The Bischler-Napieralski reaction of VI gave 3, 4-dihydroisoquinoline compound (VII), reduction of its methiodide with sodium borohydride, and demesylation of its product finally gave the objective 7-benzyloxy-1, 2, 3, 4-tetrahydro-1-(p-hydroxybenzyl)-6-methoxy-2-methylisoquinoline (I) as colorless needles, m.p. 139.5∼141°. On the other hand, the amide compound (XII) was prepared by the Schotten-Baumann reaction of the amine (III) and the acid chloride (XI) and derived through the route shown in Chart 2 to 7-benzyloxy-1, 2, 3, 4-tetrahydro-1-(p-hydroxyphenyl)-6-methoxy-2-methylisoquinoline (II) as colorless plates, m.p. 166-167°. The melting points of the compounds (VII, VIII, IX, and XI) given in the preceding paper were erroneously given the melting points of XII, XIII, XV, and II in Chart 2, and the values are corrected herein.
