Benzyl Chloride → 8-Benzyl-8-azabicyclo[3.2.1]octan-3-one oxime

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Reaction Steps

Sodium hydroxide (74 gm) was added to water (150 ml) at reflux under stirring. Nortropinone hydrochloride (100 gm) was added to the solution and stirred for 20 minutes, and then added benzyl chloride (94 gm) and tetrahydrofuran (300 ml). The contents were heated to reflux and maintained for 15 hours at reflux. The contents were cooled to room temperature and then added hydroxylamine hydrochloride (72 gm) at room temperature. The contents were maintained for 3 hours at room temperature and then added water (200 ml). Sodium hydroxide solution (40%, 50 ml) was added to the reaction mass and then the layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried with sodium sulphate to obtain a crude solid. The crude solid was dissolved in n-hexane (300 ml) and stirred for 1 hour. The separated solid was filtered and dried to obtain 134 gm of 8-benzyl-8-azabicyclo[3.2.1]octan-3-one oxime.

Provenance & Evidence