Water → 7-Trifluoromethyl-8-chloro-10-(4-methylpiperazino)dibenzo(b,f)thiepine

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Reaction Steps

1-Methylpiperazine (8.0 g) was added to a solution of 7-trifluoromethyl-8-chlorodibenzo(b,f)thiepine-10(11H)-one (the preparation of which is described in the preceding Example) (5.17 g) in benzene (40 ml). Then, titanium tetrachloride (1.63 g) in benzene (10 ml) was added dropwise, the mixture refluxed for 24 hours while stirring, cooled and decomposed with water (60 ml). The separated solid was filtered and washed with benzene and water. The benzene layer of the filtrate was separated, washed with water, filtered with charcoal and dried over magnesium sulfate. Evaporation of the benzene yielded 5.68 g (88%) of the crude enamine base, named in the heading of this Example. Neutralization of this base with methanesulfonic acid in ethanol, followed by addition of ether, yielded the crystalline methanesulfonate which crystallized from acetone as a monohydrate; m.p. 267°-270° C.

Provenance & Evidence