Acetic Acid → 3-(2-Adamantyl)-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline

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Reaction Steps

Following the procedure of Example 1, step 3, 5.00 g (34.7 mmol) of 1-methyl-3,4-dihydronaphthalene in 35 ml of acetic acid was reacted with 11.3 ml of 37% formaldehyde solution and 14.96 g of 2-adamantanamine hydrochloride. Work up gave 14.47 g of crude 3-(2-adamantyl)-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline. Following the procedure of Example 2, this was reacted with 2.09 g of lithium wire in 500 ml of liquid ammonia, 200 ml of anhydrous THF and 5 ml of aniline. Chromatography on flash silica, eluting with 2-10% methanol/dichloromethane, then on alumina, eluting with 0-4% ethyl acetate/petroleum ether, gave 2.73 g (24%) 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/petroleum ether, the title product hydrochloride was obtained as a white solid, m.p. 247°-252° C. NMR δ(D2O/CD3CN) 1.52 (1H, m), 1.69-1.98 (15H, m), 2.48 (2H, s), 2.59-2.75 (3H, m), 2.91-3.09 (3H, m), 3.29-3.34 (1H, m), 3.79 (1H, m), 3.95 (1H, m), 7.18-7.24 (3H, m), 7.30-7.33 (1H, m). m/z (CI+, NH3) 322 (M+H)+.

Provenance & Evidence