Antidepressant 1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]-cyclohepten-6-substituted oximes

A process for preparing a compound of the formula:

• ##STR27## where X or Y = H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, CH.sub.3 S, CH.sub.3 SO.sub.2, SO.sub.2 N(CH.sub.3).sub.2, provided that one is H;
• Z = c.sub.2 -c.sub.3 alkylene;
• R.sub.1 and R.sub.2 independently = H, C.sub.1 -C.sub.4 alkyl, or together can form a ring with N:
• ##STR28## in which W can be
• --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, or
• --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --;
• which comprises contacting a compound of the formula:
• ##STR29## where M is an alkali metal;
• with a compound of the formula:
• ##STR30## where Hal is a halogen in an inert anhydrous solvent at a temperature of about 10.degree.-50.degree. C.