Bromomethylcyclopropane → HCID 54381315, compound

Participants

Reaction Steps

To a solution of 0.200 g (1.07 mmol) of trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in anhydrous dichloromethane (20 ml) was added 0.200 g (1.48 mmol) of (bromomethyl)cyclopropane and the reaction mixture was left to stand for 24 h. The solvent was removed in vacuo and the residue was chromatographed on flash silica, eluting with 10% methanol/dichloromethane to give 0.160 g (62%) of the title product as an oil. The hydrochloride salt was made using etheral hydrogen chloride. Upon evaporation of the solvent, washing with ether and recrystallisation from ethanol/ethyl acetate/petroleum ether, the title product hydrochloride was obtained as a white sold, m.p. 255°-257° C. NMR δ(D2O) 0.43 (2H, m), 0.78 (2H, m), 1.17 (1H, m), 1.58 (1H, m), 1.80-1.94 (2H, m), 2.67-2.77 (2H, m), 2.90-2.97 (3H, m), 3.09 (2H, d, J=7.4 Hz), 3.20 (1H, t of d, J=13.1 and 3.0 Hz), 3.74 (1H, m), 3.87 (1H, m), 7.22-7.31 (3H, m), 7.36-7.38 (1H, m). m/z (CI+, NH3) 242 (M+H)+, 182, 165.

Provenance & Evidence