Acetic Acid → 3-(1-Adamantyl)-1,2,3,4,5,6-hexahydrobenz[f]isoquinoline

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Following the procedure of Example 1, step 3, 2.05 g (14.0 mmol) of 1-methyl-3,4-dihydronaphthalene in 14 ml of acetic acid was reacted with 4.54 ml of 37% formaldehyde solution and 6.03 g of 1-adamantanamine hydrochloride. Work up gave 5.58 g of crude 3-(1-adamantyl)-1,2,3,4,5,6-hexahydrobenz[f]isoquinoline. Following the procedure of Example 2, this was reacted with 1.02 g of lithium wire in 400 ml of liquid ammonia, 100 ml of anhydrous THF and 2 ml of aniline. Chromatography on flash silica, eluting with 5-20% methanol/dichloromethane, then on alumina, eluting with 2-7% ethyl acetate/petroleum ether, afforded 0.54 g (12%) 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 methanol/petroleum ether, the title product hydrochloride was obtained as a white solid, m.p. 252°-255° C. NMR δ(D2O, CD3CN) 1.56 (1H, m), 1.68-1.92 (9H, m), 2.02-2.04 (6H, m), 2.27 (3H, s), 2.61 (1H, m), 2.74 (1H, d of d), 2.82 (1H, t, J=12.0 Hz), 2.92-2.95 (2H, m), 3.08 (1H, t of d), 3.65 (1H, m), 3.82 (1H, m), 7.19-7.23 (3H, m), 7.29-7.30 (1H, m). m/z (CI+, NH3) 322 (M+H)+, 195. Analysis calcd. for C23H32ClN: C, 77.17; H, 9.01; N, 3.91%. Found: C, 77.09; H, 8.95; N, 3.89%.

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