In an attempt to find new antihistaminics of the Antergan type, the Beckmann rearrangement reaction was applied to 3, 4-methylenedioxy-α-dimethylaminopropiophenone oxime (IV) and α-piperidino derivative (VII), expecting the amide (VIII) and its analogs as the rearrangement products. 3, 4-Methylenedioxybenzonitrile (V), however, was obtained in nearly quantitative yield, either in chloroform-thionyl chloride or ether-phosphorus pentachloride procedure. A small amount of piperidine, but not dimethylamine, was traced in the reaction product as its picrate, the second half of the molecule of the oxime being largely converted into viscous, unidentifiable substance, probably a vinylamino polymer. The result is more or less simil ar to that of the Beckmann rearrangement of the second order. The action of toluenesulfonyl chloride upon the oxime in the presence of alkali again gave (V), but toluenesulfonyl chloride alone in pyridine or alkali solution (potassium hydroxide) only ended in recovery of the oxime.

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