Modified syntheses of 2-(methylthio)-10-(2-(1-methyl-2-piperidinyl) ethyl) phenothiazine (thioridazine) and 1-(3-(2-(methylsulfonyl)-10-phenothiazinyl) propyl)- …

K Šindelář, J Holubek, I Koruna…

Index: Sindelar, Karel; Holubek, Jiri; Koruna, Ivan; Hrubantova, Marta Collection of Czechoslovak Chemical Communications, 1990 , vol. 55, # 6 p. 1586 - 1601

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Abstract

Abstract Modified syntheses of the title compounds used the enhanced reactivity of the aromatic fluorine atom in exchange reactions and proceeded via fluorinated intermediates. 2- (2-Fluorophenylthio)-5-(methylthio) nitrobenzene (III) was synthesized, reduced to the amine IV which was alkylated with 2-(2-chloroethyl)-1-methylpiperidine to compound VI. This was cyclized with sodium hydride in dimethyl sulfoxide to thioridazine (I) in excellent yield. The ...