Piperazinobutyrophenone derivatives

Details Piperazinobutyrophenone derivatives Piperazinobutyrophenone derivatives

1973-01-22

1976-01-20

Gallagher, Richard J.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260240G, 260268BC, 260268R, 424250, C07D29512

Patent

active

039338240

ABSTRACT:
Central nervous system active butyrophenone derivatives in which .gamma. -piperazinobutyrophenone derivatives of the formula, ##SPC1##
Wherein R.sup.1 is hydrogen, amino, C.sub.1 -C.sub.5 alkanoylamino, C.sub.1 -C.sub.4 alkylamino or N-(C.sub.1 -C.sub.4 alkyl)(C.sub.1 -C.sub.5 alkanoyl) amino; R.sup.2 is hydrogen or halogen; R.sup.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or trifluoromethyl; and m is 0, 1 or 2, and acid addition salts thereof, can be prepared by reacting an indole derivative of the formula, ##SPC2##
Wherein R.sup.2, R.sup.3 and m are the same as defined above, and R.sup.4 and R.sup.5 are hydrogen or C.sub.1 -C.sub.4 alkyl respectively, with an oxidizing agent to yield an o-alkanoylamino-.gamma.-piperazinobutyrophenone derivative of the formula, ##SPC3##
Wherein R.sup.2, R.sup.3, R.sup.4, R.sup.5 and m are the same as defined above, and further, if necessary, hydrolyzing the product to yield an o-amino-.gamma.-piperazinobutyrophenone derivative of the formula, ##SPC4##
Wherein R.sup.2, R.sup.3, R.sup.5 and m are the same as defined above, and further diazotizing, if desired, in case R.sup.5 is hydrogen, the obtained o-amino-.gamma.-piperazinobutyrophenone derivative and subsequently decomposing the resultant diazonium compound to replace the diazonium group by hydrogen. Among the butyrophenone derivatives thus obtained, those in which R.sup.1 is amino, alkanoylamino, alkylamino or N-alkylalkanoylamino and those in which R.sup.1 is hydrogen and R.sup.2 is halogen substituted at meta-position to carbonyl group are novel compounds.

REFERENCES:
patent: 2997472 (1961-08-01), Janssen
patent: 3538091 (1970-11-01), de Stevens
patent: 3562277 (1971-02-01), Hansen et al.
patent: 3637704 (1972-01-01), Umemoto et al.
patent: 3658821 (1972-04-01), Fauran et al.

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