A series of 1-substituted 2,3-polymethyleneindoles was prepared and examined for central nervous system activity. A number of these compounds wrere found to be active as antidepressants. The required 2,3-polymethyleneindoles were prepared by suitable modifications of the Fischer indole synthesis from arylhydrazines and alicyclic ketones. These were converted to N-substituted derivatives by various methods.
The reaction of unsubstituted aliphatic nitriles, such as acetonitrile and benzonitrile, with amines in water is catalyzed by such different compounds as hydrochloric acid, acetic acid, and thiophenol and is particularly well catalyzed by hydrogen sulfide and thioacetamide. The hydrogen sulfide catalysis leads to either substituted amides (with primary amines at 100-150°, with morpholine at 100-150°, and with piperidine and diethylamine at 150°) or unsubstituted amides (with piperidine and diethylamine at 100°). These products are not produced in substantial amounts in uncatalyzed reactions at these temperatures. The reaction of acetonitrile with water in the presence of triethylamine and hydrogen sulfide at 100°g ives acetamide.
Reinvestigation of the Mannich Reaction Na2SO,, and evaporated under reduced pressure. The residue was extracted with hexane and the hexane solution was eluted from a silicic acid-Celite10 column by use of a hexane (3 vol)benzene (7 vol) mixture. Evaporation of the second fraction gave 0.20 g (6%) of white crystalline 1-adamantyl azide: mp
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