Benzyl Bromide → HCID 54124531, compound

Participants

Reaction Steps

Following the procedure of Example 3, step 4, 40.0 mg (0.214 mmol) of trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in anhydrous DMF (2 ml) was reacted with 32.5 mg (0.235 mmol) of anhydrous potassium carbonate and 25.4 ml (0.214 mmol) of benzyl bromide. Chromatography on flash silica, eluting with 10-15% ethyl acetate/petroleum ether, gave 32.0 mg (54%) of the title product as a white solid. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent the title product hydrochloride was obtained as a white solid, m.p. 244°-248° C. (dec). NMR δ(D2O) 1.49-1.84 (4H, m), 2.68 (2H, m), 2.89-2.99 (3H, m), 3.23 (1H, m), 3.53 (1H, m), 3.73 (1H, m), 4.37 (2H, m), 7.23-7.27 (3H, m), 7.33 (1H, m), 7.54 (5H, s). m/z (CI+, NH3) 278 (M+H)+, 186 (M-CH2Ph)+, 184, 110.

Provenance & Evidence