Synthesis
To a solution of 4-(3-nitrophenyl)morpholine (43) (4.16 g, 20 mmol) in methanol (50 mL) cooled to 0 °C in an ice water bath was added 10% palladium/carbon catalyst (460 mg). The reaction mixture was stirred at room temperature and under hydrogen atmosphere (1 atm) for 16 hours. Upon completion of the reaction, the catalyst was removed by filtration through diatomaceous earth (Celite). The filtrate was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 3-(4-morpholinyl)aniline (3.39 g, 95.2%) as an orange solid. The product was analyzed by LC-MS showing m/z(ESP): 179 [M+H] and retention time (R/T) of 1.69 min, which is sufficiently pure to be used in subsequent reactions without further purification.
References
[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 26, p. 8261 - 8269
[2] Patent: US2006/199804, 2006, A1. Location in patent: Page/Page column 31
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 407 - 416
[4] Patent: WO2007/339, 2007, A1. Location in patent: Page/Page column 52
[5] Patent: WO2003/90912, 2003, A1. Location in patent: Page/Page column 76
