Hydrazine hydrate (1:1) → 5-Fluoro-4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)aniline

Participants

Reaction Conditions

Reaction Steps

To 1-[2-fluoro-5-(methyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine (2.0 g, 6.7 mmol) in MeOH (100 mL) was added iron (III) chloride (0.3 g, 2.0 mmol) and actived carbon (2.0 g). The reaction mixture was stirred at 64° C. for 20 min before the dropwise addition of hydrazine hydrate (4.0 mL, 80.7 mmol) over 5 min. The reaction was kept stirring at 64° C. for additional 4 h. Filtration, concentration of the residue, and purification via column chromatography on SiO2 (0-10% 2 M NH3 in MeOH/DCM) afforded 5-fluoro-4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)aniline as a dark brown solid (1.7 g, 95% yield). 1H NMR (400 MHz, DMSO-d6) 5 ppm 0.96 (d, J=6.6 Hz, 6 H), 2.45-2.54 (m, 4 H), 2.62 (dt, J=13.0, 6.6 Hz, 1 H), 2.79-2.86 (m, 4 H), 3.69 (s, 3 H), 4.55 (s, 2 H), 6.38 (d, J=13.6 Hz, 1 H), 6.49 (d, J=8.2 Hz, 1 H).

Provenance & Evidence