(Chloromethyl)cyclopropane → 3-Acetyl-N-(cyclpropylmethyl)morphinan

Participants

Reaction Steps

To a mixture of 0.8 g of (-)-1-(morphinan-3-yl)-ethanone, 0.6 g of sodium bicarbonate and 10 ml dimethylformamide, was added 0.3 g of cyclopropylmethyl chloride. After the mixture had been heated at reflux for 18 hours, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in 60 ml ether. The ether solution was washed with water, dried over magnesium sulfate and removal of the solvent gave 0.8 g (83%) of crude (-)-1-[N-(cyclopropylmethyl)morphinan-3-yl]ethanone. For analysis, a sample of this compound was distilled, bp 185°-195° (0.1 mm), [α]25D-83.21° (c 1.02, MeOH).

Provenance & Evidence