2-Methoxybenzylamine → 1-[(2-Methoxyphenylmethyl)amino]-6,7-dimethoxyisoquinoline hydrochloride

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Reaction Steps

6,7-Dimethoxy-1-chloroisoquinoline (J. Am. Pharm. Assoc., Sci. Ed. (1952), 41, 643-50; C.A. 47, 11205d.) (1.0 gm, 0.00447 mol) and 2-methoxybenzylamine (1.22 gm, 0.00894 mol) were mixed at room temperature and heated, with stirring, in an oil-bath at 140° for 1.5 hours. After cooling the mixture was dissolved in chloroform and the solution washed with saturated NaHCO3 solution and water, dried and evaporated. The resulting oil was chromatographed on silica gel, using chloroform as eluent. Fractions were monitored by t.l.c. and those containing pure product were combined, evaporated to dryness and the residue (0.25 g) dissolved in ethanol containing ethanolic hydrogen chloride. This solution was evaporated to dryness and the residue crystallised from ethanol/diethyl ether to give the title compound as its hydrochloride salt (0.22 gm), m.p. 225°-229°.

Provenance & Evidence