Ammonia → HCID 53876213, compound

Participants

Reaction Steps

Following the procedure of Example 2, 0.64 g (2.71 mmol) of 1,2,3,4,5,6-hexahydro-3-methyl-benz[f]isoquinoline hydrochloride was reacted with 0.126 g of lithium wire in 100 ml of liquid ammonia, 25 ml of anhydrous THF and 0.25 ml of aniline. Chromatography on flash silica, eluting with 5-10% methanol/dichloromethane, then on alumina, eluting with 25% ethyl acetate/petroleum ether gave 0.340 g (62%) of the title product as a colourless oil. 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. 277°-285° C. (dec). NMR δ(D2O) 1.52-1.92 (4H, m), 2.63-2.75 (2H, m), 2.86-2.98 (3H, m), 2.92 (3H, s), 3.19 (1H, t of d, J=13 and 3 Hz), 3.56 (1H, m), 7.22-7.28 (3H, m), 7.33-7.36 (1H, m). m/z (CI+, NH3) 202 (M+H)+.

Provenance & Evidence