Hydrazine hydrate (1:1) → 2-(Methyloxy)-4-(4-propyl-1-piperazinyl)aniline

Participants

Reaction Steps

A solution of 1-[3-(methyloxy)-4-nitrophenyl]-4-propylpiperazine (Intermediate B50, 1.5 g, 5.4 mmol), FeCl3 (0.300 g, 1.85 mmol), activated carbon (2.0 g), and hydrazine hydrate (2.1 mL, 65 mmol) was heated in methanol (50 mL) for 3 hours. The mixture was filtered over celite and concentrated to give 2-(methyloxy)-4-(4-propyl-1-piperazinyl)aniline as a white solid (1.03 g, 4.2 mmol, 78% yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.93 (t, J=7.51 Hz, 3 H), 1.51-1.61 (m, 2 H), 2.37 (d, J=8.06 Hz, 2 H), 2.57-2.66 (m, 4 H), 3.09-3.10 (m, 4 H), 3.53 (s, 2 H), 3.83 (s, 3 H), 6.42 (dd, J=8.24, 2.38 Hz, 1H), 6.52 (d, J=2.20 Hz, 1 H), 6.64 (d, J=8.42 Hz, 1 H).

Provenance & Evidence