Process for preparation of 1,4-benzodioxane derivative

C - Chemistry – Metallurgy – 07 – D

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C07D 319/20 (2006.01) C07D 319/22 (2006.01) C07D 493/04 (2006.01)

Patent

CA 2215604

The present invention is directed to a novel process for preparing a 1,4-benzodioxane derivative of the formula (1) Image wherein, R1 is H, RSO2 in which R is alkyl, phenyl which may be substituted with alkyl, R2, R3, R4 are H, halogen, OH, nitro, cyano, formyl, COOH, alkoxycarbonyloxy, alkyl, alkoxy, haloalkyl, N,N-dialkylamino, alkylcarbonyl, alkoxycarbonyl, phenyl which may be substituted. The 1,4-benzodioxane derivative is a useful intermediate in the preparation of circulatory drugs and drugs for psychoneurosis. The process comprises sulfonating a phenoxypropanediol with a sulfonyl halide, eliminating the protective group, and then cyclizing the sulfonated compound by treating with a base followed by, if necessary, further sulfonation.

L'invention porte sur une nouvelle technique de production de dérivés de 1,4-benzodioxane de formule (1) qui se sont révélés utiles en tant qu'intermédiaires dans l'élaboration de remèdes contre des maladies circulatoires et psychonévrotiques. Le procédé consiste à sulfoner un composé de phénoxypropanediol par réaction avec un composé d'halogénure de sulfuryle, à éliminer le groupe protecteur, à traiter avec une base aux fins d'une exposition à une réaction de cyclisation, suivie, si nécessaire, d'une autre sulfonation. Dans la formule générale (1), R<1> représente H ou RSO2 (où R représente un alkyle ou éventuellement un phényle substitué par un alkyle); R<2>, R<3> et R<4> représentent chacun H, halogéno, OH, NO2, CN, formyle, COOH, alcoxycarbonyloxy, alkyle, alcoxy, haloalkyle, N, N-dialkylamino, alkylcarbonyl, alcoxycarbonyl, éventuellement un phényle substitué par un alkyle, etc.

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