9-hydroxy-1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine derivatives as analgesics

Three 1,3-dimethyl-9-hydroxy-1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine derivatives (7-9) have been synthesized and tested as analgesics. The synthesis of these compounds involved conversion of 1-methyl-7-methoxy-beta-tetralone (1) by Mannich reaction with MeNH2 and HCHO to give the 11-ketone 2, from which 7,8, and 9, respectively, were obtained. These compounds have analgesic activity, and 7 was found to be comparable to codeine.