DIHYDRO-N-norGELSEMINE AND SOME OF ITS DERIVATIVES

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Abstract
Treatment of gelsemine with cyanogen bromide produced N-cyano-norgelsemine which on catalytic hydrogenation gave rise to N-cyanodihydro-N-norgelsemine, identical with the product of the reaction of cyanogen bromide with dihydrogelsemine. N-Cyanodihydro-N-norgelsemine was hydrolyzed with hydrochloric acid to dihydro-N-norgelsemine which readily formed a mono- or a dibenzoyl derivative according to the conditions, and a p-toluenesulphonamide. The action of phosphorus pentachloride on the monobenzoyl derivative gave rise to N-benzoylchlorodihydro-N-norgelsemine, hydrolyzable by hydrochloric acid to chlorodihydro-N-norgelsemine. This chloro compound was converted by the action of formaldehyde and formic acid to chlorodihydrogelsemine, identical with the product of the action of phosphorus pentachloride on dihydrogelsemine. Chlorination of dihydrogelsemine with chlorine produced dichlorogelsemine.

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