In order to test the analgesic action of 3, 4, 5, 6-tetrahydro-2H-1, 5-methanobenzo[e]-[1, 4]diazocin (XXI), methods for its synthesis was examined using various starting materials. Compounds (XI to XIII) were synthesized from 3-bromoquinoline (V). Their derivation to XIV or synthesis of XXI by reduction of V was tried but the objective was not attained. Finally, V was derived to XXI by amination, benzoylation, N-alkylation by ethyl chloroacetate, and reduction to the lactam (XX), and its reduction with lithium aluminum hydride (method d). XXI was also obtained from XV by the route shown in Chart 2.
