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Synthesis of the N -Oxides of Phenothiazine Antipsychotic Agents

Journal of Pharmaceutical Sciences, ISSN: 0022-3549, Vol: 82, Issue: 3, Page: 330-333
1993
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Chlorpromazine N-oxide, fluphenazine N 4 ’-oxide, prochlor-perazine N 4 ’-oxide, sulforidazine N -oxide, and trifluoperazine N 4 ’-oxide were synthesized by oxidation of the designated nitrogen atom in the N- 10 side chain of the respective parent drug with 3-chloroperoxybenzoic acid. In the case of trifluoperazine, a stepwise increase in the amount of oxidant yielded the N 1,N 4 -dioxide and N 1 ’, N 4 ’,S-trioxide. The N’,S- dioxides of chlorpromazine and sulforidazine were obtained by hydrogen peroxide oxidation of the appropriate parent drug.

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