Reaction Steps
6-Methoxy-1-methyl-7-[(2S,3S)-(2-phenyl-piperidin-3-ylamino)-methyl]-3,4-dihydro-1H-quinolin-2-one (100 mg, 0.26 mmol) and 2-iodopropane (0.058 mL, 0.58 mmol) were stirred in acetonitrile at 60° C. for 2 days. The reaction was diluted with methylene chloride, washed once with satd. NaHCO3, dried over MgSO4, filtered, and concentrated. Silica gel chromatography using (9.1 ethyl acetate/methanol) gave 38 mg (34%) of the title compound, a yellow oil. Rf=0.08 (9:1 ethyl acetate/methanol). MS (M+H)+=422.1; 1H NMR (400 MHz, CDCl3): δ 0.66–0.68 (d, J=6.5 Hz, 3H), 1.00–1.02 (d, J=6.5 Hz, 3H), 1.35–1.42 (m, 1H), 1.50–1.53 (bd, J=13.0 Hz, 1H), 1.91–1.97 (m, 1H), 2.02–2.07 (m, 1H), 2.22–2.28 (t, J=11.5 Hz, 1H), 2.53–2.57 (t, J=7.4 Hz, 2H), 2.64 (s, 1H), 2.75–2.79 (t, J=7.4 Hz, 2H), 2.94–3.02 (m, 2H), 3.12 (s, 3H), 3.38–3.42 (d, J=14.6 Hz, 1H), 3.54 (s, 3H), 3.60 (s, 1H), 3.66–3.69 (d, J=14.6 Hz, 1H), 6.49 (s, 1H), 6.66 (s, 1H), 7.19–7.29 (m, 3H), 7.36–7.38 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 12.0, 20.3, 21.1, 25.5, 27.7, 29.6, 31.8, 44.1, 45.0, 48.5, 55.5, 56.3, 109.8, 112.8, 116.0, 124.9, 126.7, 127.8, 129.2, 133.5, 141.5, 152.9, 170.0. The dihydrochloride salt was prepared by the addition of 2 M HCl in ether to a solution of the product in ethyl acetate. Concentration gave a white solid.
