Process for preparing aryl piperazinyl-heterocyclic compounds

A process for preparing a compound of the formula:

• ##STR8## or a pharmaceutically acceptable acid addition salt thereof, wherein Ar is naphthyl optionally substituted by fluoro, chloro, trifluoromethyl, methoxy, cyano or nitro;
• quinolyl;
• 6-hydroxy-8-quinolyl;
• isoquinolyl;
• quinazolyl;
• benzoisothiazolyl or an oxide or dioxide thereof, each optionally substituted by fluoro, chloro, trifluoromethyl, methoxy, cyano, or nitro;
• benzothiazolyl;
• benzothiadiazolyl;
• benzotriazolyl;
• benzoxazolyl;
• benzoxazolonyl;
• indolyl;
• indanyl optionally substituted by one or two fluoro;
• 3-indazolyl optionally substituted by 1-trifluoromethylphenyl;
• or phthalazinyl;
• n is 1 or 2;
• and
• X and Y together with the phenyl to which they are attached form quinolyl;
• 2-hydroxyquinolyl;
• benzothiazolyl;
• 2-aminobenzothiazolyl;
• benzoisothiazolyl;
• indazolyl;
• 2-hydroxyindazolyl;
• indolyl;
• spiro[cyclopentane-1,3'-indolinyl-indolinyl];
• oxindolyl optionally substituted by one to three of (C.sub.1 -C.sub.3)alkyl, or one of chloro, fluoro or phenyl, said phenyl optionally substituted by one chloro or fluoro;
• benzoxazolyl;
• 2-aminobenzoxazolyl;
• benzoxazolonyl;
• 2-aminobenzoxazolinyl;
• benzothiazolonyl;
• benzoimidazolonyl;
• or benzotriazolyl;
• which comprises reacting a monosubstituted piperazine of the formula ##STR9## wherein AR is as defined above, with an alkyl halide containing compound of the formula ##STR10## wherein n, X and Y are as defined above and Hal is fluoro, chloro, bromo or iodo, in water with a reagent to neutralize the hydrohalic acid and refluxing the mixture under conditions which are suitable to effect the coupling of said monosubstituted piperazines with said alkyl halide containing compound and, if desired, preparing the corresponding pharmaceutically acceptable acid addition salt.