Phenylethanolamine → N-{4-[4-(2-Hydroxy-2-phenyl-ethylamino)-piperidin-1-yl]-phenyl}-4-methoxy-benzenesulfonamide

Participants

Reaction Steps

A mixture of 4-methoxy-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 218) (0.16 g, 0.44 mmol) and 2-amino-1-phenylethanol (0.18 g, 1.3 mmol) in 75 mL of methanol was hydrogenated in the presence of 100 mg of 10% Pd/C under H2 (5˜20 psi) for overnight. The catalyst was then removed by filtering through a short pad of silica gel. The filtrate was concentrated and purified by silica gel chromatography using 5-10% MeOH/CH2Cl2 as eluent to give 0.13 g (61%) of the title compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2H), 1.78-1.92 (m, 2H), 2.50-2.80 (m, 5H), 3.60-3.70 (m, 2H), 3.79 (s, 3H), 4.56-4.60 (m, 1H), 5.26 (brs, 1H), 6.76 (d, J=9.0 Hz, 2H), 6.86 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 2H), 7.20-7.25 (m, 1H), 7.25-7.36 (m, 4H), 7.58 (d, J=9.0 Hz, 2H); MS (ES) m/z: 482.4 (MH+); HRMS Calcd. for C26H31N3O4S(M+): 481.2035. Found: 481.2028.

Provenance & Evidence