1-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine → 4-(4-Isopropylpiperazin-1-YL)-2-methoxyphenylamine

Participants

Reaction Steps

In a pressure vessel was placed a solution of 1-(1-methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine (4.0 g, 14.3 mmol) in EtOH (100 mL). The solution was purged with N2 for 15 min before the addition of 10% Pd/carbon (0.5 g). The reaction was stirred at rt for 5 h under 60 psi H2. After releasing H2 pressure, filtration removed the solid resin, and the filtrate was concentrated and purified with silica gel chromatography to furnish the title compound of step B (3.6 g, 99% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.09 (d, J=6.6 Hz, 6H), 2.66-2.75 (m, 5H), 3.05-3.10 (m, 4H), 3.47 (s, 3H), 3.83 (s, 2H), 6.42 (dd, J=8.2, 2.4 Hz, 1H), 6.52 (d, J=2.2 Hz, 1H), 6.64 (d, J=8.4 Hz, 1H).

Provenance & Evidence