反应详情

A mixture of 1-[3-(ethyloxy)-4-nitrophenyl]-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}-piperazine (290 mg, 0.65 mmol) and platinum (sulfided, 5 wt. % on carbon, 50 mg, 0.013 mmol) in 20% MeOH/EtOAc (20 mL) was added to a high-pressure hydrogenation reaction flask. The reaction was purged with N2 and vacuum (3×). The reaction was purged with H2 and vacuum (3×). The reaction was then treated with H2 at 50 psi and stirred for approximately 20 h. The reaction was degassed, then poured through a Teflon filter, washing the solid with MeOH and DCM. The filtrate was concentrated under vacuum to give the title compound of step B (256 mg, 0.62 mmol, 97%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 6.50 (d, 1H, J=8.43 Hz), 6.44 (d, 1H, J=2.38 Hz), 6.26 (cd, 1H, J=2.38 and 8.43 Hz), 4.17 (br s, 2H), 3.95 (q, 2H, J=6.96 Hz), 3.25 (t, 2H, J=6.69 Hz), 3.01 (s, 3H), 2.91 (M, 6H), 2.65 (t, 2H, J=6.78 Hz), 2.57 (m, 4H), 2.10-2.20 (m, 1H), 1.89-1.97 (m, 2H), 1.76 (m, 2H), 1.28-1.32 (m, 5H).

1. additionwas added to a high-pressure hydrogenation reaction flask
2. customThe reaction was purged with N2 and vacuum (3×)
3. customThe reaction was purged with H2 and vacuum (3×)
4. additionThe reaction was then treated with H2 at 50 psi
5. customThe reaction was degassed
6. additionpoured through a Teflon
7. filtrationfilter
8. washwashing the solid with MeOH and DCM
9. concentrationThe filtrate was concentrated under vacuum