Dimethylformamide → HCID 70168185, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of cesium carbonate (1.09 g), cis-2-(N-benzylmethylamino)methyl-6-hydroxy-1-phenyl-1,2,3,4-tetrahydronaphthalene (600 mg) and N,N-dimethylformamide (10 cm3) was added benzyl bromide (0.236 cm3). The resulting mixture was warmed to 80° C. and stirred for 2 h. Upon cooling, water (50 cm3) was added and the aqueous mass was extracted with ether (2×50 cm3). The combined ether extracts were washed with water (30 cm3), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure to afford a yellow oil. This was purified by column chromatography [silica, eluting with petroleum ether (b.p. 40-60° C.)-ethyl acetate (15:1)] to afford the title compound (538 mg; 72%) as a light yellow oil.

Provenance & Evidence