反应详情

8-Benzyl-3-(4-chlorophenyl)-3,8-diazabicyclo[3.2.1]octane (8.5 g, 27.17 mmol) and 10% palladium on carbon (8.5 g) were combined in 1N hydrochloric acid/methanol (600 ml). The mixture was hydrogenated at atmospheric pressure for 4 hours under hydrogen gas. The reaction was filtered through Celite and the filtrate was concentrated to yield 3-(4-chlorophenyl)-3,8-diazabicyclo[3.2.1]octane hydrochloride (7.0 g, 100%) as an off-white solid. A portion recrystallized from water yielded white crystalline flakes which had the following properties: M.p. 270-275° C.; 1H NMR (CDCl3) δ: 9.70 (brd s, 2H), 7.22 (d, J=9.1 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 4.06 (brd s, 2H), 3.55 (d, J=11.6 Hz, 2H), 3.12 (d, J=12 Hz, 2H), 2.01-1.79 (m, 4H); IR (KBr): 3969, 3913, 3862, 3739, 3670, 3194, 3094, 2990, 2972, 2947, 2867, 2778, 2748, 2696, 2657, 2609, 2574, 2537, 2500, 2431, 2396, 2384, 2252, 2133, 2092, 2078, 2033, 1991, 1951, 1922, 1903, 1873, 1799, 1750, 1688, 1600, 1570, 1500, 1460, 1421, 1383, 1367, 1344, 1323, 1269, 1252, 1220, 1207, 1165, 1155, 1120, 1099, 1079, 1059, 1012, 1001, 978, 937, 922, 904, 872, 828, 817, 808, 783, 749, 700, 651, 632, 534, 520, 468, 415, 403, (cm−1); Elemental Analysis, Calculated for C12H16CIN2: C, 55.61; H, 6.23; N, 10.81; Found: C, 55.35, H, 6.21, N, 10.79.

1. filtrationThe reaction was filtered through Celite
2. concentrationthe filtrate was concentrated