Synthèse d'analogues partiellement saturés de l'amitriptyline à partir d'ortho‐tolunitriles. 2e Communication sur les antidépresseurs et les neuroleptiques tricycliques [1]

Substituted o‐tolunitriles are alkylated with 1‐bromomethyl‐cyclohexene. Saponification yields substituted o‐[2‐(1‐cyclohexen‐1‐yl)‐ethyl]‐benzoic acids, which are cyclised to 1,2,3,4,10,11‐hexahydro‐5H‐dibenzo[a,d]cyclohepten‐5‐ones. Reaction of the latter with (3‐dimethylamino‐propyl)‐magnesium chloride yields, after dehydration, hexahydro derivatives of the known antidepressant amitriptyline. The position of the double bonds remains uncertain.