Allyl bromide → HCID 67942351, compound

Participants

Reaction Steps

Following the procedure of Example 3, step 4, 0.152 g (0.810 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in 10 ml of anhydrous DMF was reacted with 0.123 g (0.890 mmol) of anhydrous potassium carbonate and 0.074 ml (0.855 mmol) of allyl bromide. Chromatography on flash silica, eluting with 3-7% methanol/dichloromethane, then on alumina, eluting with 2-5% ethyl acetate/petroleum ether, gave 0.064 g (35%) of the title product as a colourless oil. 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. 204°-214° C. NMR δ(D2O) 1.57 (1H, m), 1.69 (1H, m), 1.80-1.92 (2H, m), 2.66-2.77 (2H, m), 2.88-2.95 (3H, m), 3.18 (1H, t, J=11.4 Hz), 3.60 (1 H, m), 3.77 (1H, m), 3.81 (2H, d, J=7.2 Hz), 5.60-5.65 (2H, m), 5.98 (1H, m), 7.22-7.29 (3H, m), 7.35-7.37 (1H, m). m/z (CI+, NH3) 228 (M+H)+. Analysis calcd. for C16H22ClN: C, 72.85; H, 8.41; N, 5.31%. Found: C, 72.84; H, 8.40; N, 5.26%.

Provenance & Evidence