Two general routes to 1,4-disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepines

[GRAPHICS] Two general routes to 1,4disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized pheneth ylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl )benzyl alcohol, while the second route utilizes the addition of a Grignard reagent to the oxazolidine derived from a substitued phenylacetaldehyde an d alpha-(methylaminomethyl)benzyl alcohol, In all cases studied, the cis-1, 4-disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepine was obtained as the maj or product.