Synthesis
General procedure: 1-(2-fluoro-4-nitrophenyl)-4-methylpiperazine (14.76 g, 61.70 mmol) was dissolved in tetrahydrofuran (THF, 80 mL) and palladium/carbon catalyst (Pd/C, 3.00 g) was added. Hydrogen (H2) was passed into the reaction mixture at room temperature and the reaction was stirred overnight. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford 3-fluoro-4-(4-methylpiperazinyl)aniline as an off-white solid (11.99 g, 93% yield).
References
[1] Patent: US2002/151554, 2002, A1
[2] Patent: WO2014/12360, 2014, A1. Location in patent: Paragraph 00293
[3] Patent: US2015/87639, 2015, A1. Location in patent: Paragraph 0550
[4] Patent: TWI607995, 2017, B. Location in patent: Page/Page column 128
[5] Journal of Medicinal Chemistry, 2008, vol. 51, # 12, p. 3507 - 3525
