Process for the preparation of 4-(1-methyl-4-...

Details Process for the preparation of 4-(1-methyl-4-... Process for the preparation of 4-(1-methyl-4-...

C - Chemistry, Metallurgy

07

D

260/279.25

C07D 495/04 (2006.01)

Patent

CA 1191138

ABSTRACT OF THE DISCLOSURE The invention relates to the field of synthetic drugs, more particularly to a process for the preparation of 4-(1-methyl-4-piperidylidene)-4,9-dihydrothieno(2,3-c)- -2-benzothiepin of formula I Image (I) and its hydrogen(+)tartrate by the reaction of thieno(2,3-c) -2-benzothiepin-4(9H)-one with 1-methyl-4-piperidylmagnesium chloride in tetrahydrofuran and subsequent acid-catalyzed dehydration of the resulting 4-(1-methyl-4-piperidyl)-4,9- -dihydrothieno(2,3-c)-2-benzothiepin-4-ol (II) including such additional operations which ensure that said alcohol II is made substantially free of the simultaneously formed 7-(1-methyl-4-piperidyl)thieno(2,3-c)-2-benzothiepin-4(9H)- one (III) and that even the last residue of compound III is eliminated from the final product I. Said additional operations make use of a better solubility of compound III in ethanol; both compound I and compound II are sparingly soluble in this solvent at ambient temperature. The pure compound of formula I can, if required, be converted to said salt by neutralization with (+)tartaric acid in aqueous ethanol. Compound I and especially its hydrogen(+)tartrate possess high antihistamine, antiserotonin, antireserpine and anticataleptic activity and, due to their low toxicity, are expected to find use in the therapy of migraine.

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