Patent Document ID: 3979390
Application ID: 05341858
Patent Flag: 1

Claim One:
1. A process for producing butyrophenone derivatives and their acid addition salts, which comprises reacting a compound of the formula: ##SPC19## with a secondary amine of the formula: ##EQU2## wherein R.sup.11 and R.sup.12 are each hydrogen, C.sub.1 -C.sub.8 alkyl, hydroxy-substituted C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.4 alkoxy substituted C.sub.1 -C.sub.8 alkyl, di(C.sub.1 -C.sub.4 alkyl) amino-substituted C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or optionally substituted aralkyl, at least one of R.sup.11 and R.sup.12 being an optionally substituted benzyl group, to give an intermediate compound of the formula: ##EQU3## wherein Ar is a group of either one of the formulas: ##SPC20## Z is a secondary amino group of either one of the formulas: ##SPC21## wherein R.sup.1 is hydrogen or hydroxyl, R.sup.2 and R.sup.3 are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or trifluoromethyl and n is a integer of 0 or 1; ##SPC22## wherein R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sup.5 and R.sup.6 are each hydrogen, halogen or C.sub.1 -C.sub.4 alkyl and the dotted line is an optional bond between the carbon atoms at the 3- and 4-positions of the piperidine ring, ##SPC23## wherein R.sup.7 is hydrogen or C.sub.1 -C.sub.4 alkyl and R.sup.8 is hydrogen, halogen, C.sub.1 -C.sub.4 or C.sub.1 -C.sub.4 alkoxy, ##SPC24## wherein R.sup.9 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or trifluoromethyl and m is an integer of 0, 1 or 2, and ##SPC25## wherein R.sup.10 is hydrogen, halogen, hydroxyl, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; and thereafter hydrogenating said intermediate compound to give the corresponding compound wherein the optionally substituted benzyl group is eliminated.