10-Hydroxy-4-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine derivatives (homobenzomorphans) as analgesics

Abstract
Six 10-hydroxy-4-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine derivatives were synthesized as potential analgesics. The synthesis of these compounds involved conversion of 4-(2-dimethylaminoethyl)-6-methoxy-.alpha.-tetralone derivatives to their N-methyl analogues and the subsequent intramolecular Mannich reaction with formaldehyde to give the 7-keto-C-ring homobenzomorphans. Some of these compounds are as potent as morphine as analgesics (mice).