2,3,4,5,6,7-hexahydro-1,6-methano-1H-3-benzazonine derivatives as analgesics

10-Methoxy- (10) and 10-hydroxy-3-methyl-2,3,4,5,6,7-hexahydro-1H-3-benzazonine (11) have been synthesized from 7-methoxy-alpha-tetralone (1) via the 1-aminomethyl compound 4, which was converted to the amino acid derivative 7. Hydrogenation and cyclization of 7 afforded the lactam 9, which was reduced with LiAlH4, followed by N-methylation to give 10, from which 11 was obtained. Compounds 10 and 11 have analgetic activity, and the former was found to be comparable to codeine.