Design and synthesis of N-[2 (2,3-dimethoxy-strychnidin-10-ylidenamino)- ethyl]-succinamic acid 4-allyl-2-methoxy-phenyl ester

In this study a brucine derivative was synthesized using several strategies. In the first stage the compound 4-(4-allyl-2-methoxy-phenoxy)-4- oxobutanoic acid (3) was obtained by the reaction of 4-allyl-2-methoxyphenol with succinic acid using N,N'-diciclohexylcarbodiimide/p-toluensulfonic acid as a catalyst. The second stage was achieved by the reaction of 3 with ethylenediamine to form 4-allyl-2-methoxyphenyl 4-[(2-aminoethyl)amino]-4- oxobutanoate (5) in presence of a carbodiimide derivative. Finally, the compound N-[2-(2,3-dimethoxy-strychnidin-10-ylidenamino)-ethyl]-succinamic acid 4-allyl-2-methoxy-phenyl ester (7) was prepared by the reaction of 3 with N ¹-(2,3-dimethoxystrychnidin-10-yliden)-ethane-1,2-diamine using as a catalyst a carbodiimide derivative. The compound 7 was also synthesized by the reaction between 5 and brucine using boric acid as a catalyst.