On the Ullmann Reaction of dl-8-Bromoarmepavine

In order to synthesize cycleanine (I) which is one of the biscoclaurine type bases, an intermediate 1-(4-hydroxybenzyl)-2-methyl-8-bromo-6, 7-dimethoxy-1, 2, 3, 4-tetra-hydroisoquinoline (dl-8-bromoarmepavine) (III) was prepared. An attempted Ullmann reaction of III failed to give I but two products, dl-armepavine (XIII), and dl-N, O, O-trimethylcoclaurine (dl-O-methylarmepavine) (XIV) were isolated from the reaction mixture. The former was formed by the dehalogenation while the latter by dehalogenation and O-methylation of III.