Hydrochloric Acid → HCID 70569288, compound

Participants

Reaction Steps

A slurry of 3,14-dimethylmorphinan-6-one (6a) (0.24 g, 0.71 mmol), sodium bicarbonate (0.6 g, 7.14 mmol) and (±) tetrahydrofurfuryl bromide (0.4 g, 2.42 mmol) and dimethylformamide (15 ml) was heated at 110° C. for 16 hours with stirring under a nitrogen atmosphere. The mixture was filtered hot and the residue was washed with dimethylformamide (15 ml). The filtrate was distilled under vacuum (bath temperature 35° C.) and the resulting brownish material was treated with chloroform (50 ml) and water (20 ml). After separation, the aqueous layer was saturated with sodium chloride and extracted with ethyl acetate (3×20 ml) whereupon the organic extracts were combined, dried over MgSO4 and filtered. The filtrate, upon concentration, was a brownish oily solid. This material was chromatographed twice over silica gel using graded methanol/chloroform mixtures to give 0.153 g (86% theory) of a mixture of the R and S isomers of the product. A part of this material (0.03 g) was converted into the hydrochloride salt by treatment with ethereal HCl to form the title compound as a tan-colored solid.

Provenance & Evidence