6 grams of normorphine, 2.7 grams of allyl bromide, 2.65 grams of sodium
bicarbonate, and 75 cc of methanol were mixed together, and the resulting
mixture was heated under reflux with stirring for a period of about 5 1/2
hours. The reaction mixture was evaporated to dryness in vacuo, the residual
material was extracted with 60 cc of boiling chloroform, 0.5 gram of activated
charcoal was added, and the resulting mixture was filtered through a layer of
diatomaceous silica. The filter cake was washed with four 10 cc portions of boiling chloroform, and the chloroform filtrate and washings were combined
and evaporated to dryness in vacuo. The residual material was triturated with
25 cc of anhydrous ether until crystalline, the ethereal mixture was cooled,
maintained at a temperature of 3°C overnight, filtered, and the crystalline
mixture was washed with three 10 cc portions of ice-cold ether. The resulting
crystalline product was dried to give 6.0 grams of N-allylnormorphine, yield
approximately 87% of theory, according to US Patent 2,891,954.
