Potassium Carbonate → HCID 101629071, compound

Participants

Reaction Steps

Following the procedure of Example 3, step 4, 0.300 g (1.60 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in 10 ml of anhydrous DMF was reacted with 0.244 g (1.77 mmol) of anhydrous potassium carbonate and 0.243 ml (1.60 mmol) of 1-bromo-3-phenylpropane. Chromatography on flash silica, eluting with 50-100% ethyl acetate/petroleum ether and 2-10% methanol/dichloromethane, then on a Lobar column, eluting with 50% ethyl acetate/petroleum ether, gave 0.123 g (26%) of the title product as a white solid. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent and recrystallisation from ethanol/ethyl acetate, the title product hydrochloride was obtained as a white solid, m.p. 196°-201° C. NMR δ(D2O/CD3CN) 1.54 (1H, m), 1.68 (1H, m), 1.75-1.89 (2H, m), 2.08-2.15 (2H, m), 2.61-2.77 (4H, m), 2.84 (1H, t, J=12.2 Hz), 2.92 (2H, m), 3.08-3.18 (3H, m), 3.56 (1H, m), 3.71 (1H, m), 7.19-7.26 (3H, m), 7.29-7.33 (4H, m), 7.39-7.43 (2H, m). m/z (CI+, NH3) 306 (M+H)+, 200 (M-CH2CH2Ph)+.

Provenance & Evidence