T. R. Ovsepyan, P. R. Akopyan, R. R. Safrazbekyan
Dec 1, 1998
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Journal
Pharmaceutical Chemistry Journal
Abstract
4-Methoxybenzylguanidine and its sulfate were patented as monoamine oxidase (MAO) inhibitors [1]. However, our attempts to develop efficient synthetic pathways revealed that the physicochemical characteristics available in the literature concerning the structure of these compounds differ from our data and are mutually contradictory. For example, the original work of Saigo [2] reported m.p. =210-212~ for 4methoxybenzylguanidine sulfate, while the later work [3] indicated 2 1 5 216~ [3]. When we reproduced the reaction pathway from [3] (scheme 1), it was found that the product I with m.p. = 215-216~ (I) is not an individual compound but represents a mixture of two guanidine derivatives with m.p. =210-212~ (Ia) and 234-235~ (Ib). It was suggested that the stage ofanisole chloromethylation involved in scheme 1 leads to the formation of an admixture of 2methoxybenzyl chloride besides the main product, 4methoxybenzyl chloride. As a result, the final product also comprises a mixture of two isomers, 2and 4-methoxybenzylguanidine sulfates. Scheme 1