Sodium borohydride → HCID 23312196, compound

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Reaction Steps

A solution of 70 g of sodium borohydride in 150 ml of water is added dropwise, with stirring and external cooling, to a solution of 70 g of 1-methyl-4-(5-chloro-2-benzofuranyl)-pyridinium-iodide in 500 ml of methanol, the manner of addition being such that the reaction temperature does not exceed 35°. The solution is subsequently stirred for 20 hours at room temperature. The methanol is thereupon evaporated off in vacuo; the aqueous phase remaining behind is extracted twice with 500 ml of chloroform each time, the chloroform solution dried over sodium sulphate, filtered, and concentrated by evaporation. The 1-methyl-4-(5-chloro-2-benzofuranyl)-1,2,3,6-tetrahydropyridine obtained is recrystallised from hexane, and then melts at 108°-118°. The hydrochloride prepared therefrom with a solution of hydrogen chloride in ethyl acetate melts, after recrystallisation from ethyl acetate, at 266°.

Provenance & Evidence