Abstract
In order to test the analgesic action of 1, 2, 3, 4, 5, 6-hexahydro-2, 6-methanobenzo[e][1, 4]diazocine (III), tetrahydroquinoline derivative (VIII) was synthesized from 2, 4-quinolinedicarboxylic acid (V) as a starting material. Reduction of VIII with lithium aluminum hydride in dioxane gave a mixture of an objective 2-aminomethyl-1, 2, 3, 4-tetrahydro-4-quinolinemethanol (IX) and 1, 2, 3, 4-tetrahydro-4-quinolinemethanol (X), the latter of which was identical with an authentic sample prepared from the acid (V). Chlorination of IX with phosphoryl chloride, followed by cyclization with potassium carbonate in xylene, gave the objective compound (III), which was derived to XIV by benzoylation.
