General procedure: 4-(4-nitrophenylethyl)morpholine (2 g, 8.46 mmol) was mixed with 500 mg of Pd/C catalyst in 100 mL of methanol and the reaction was stirred at 45 psi hydrogen pressure for 16 hours. Upon completion of the reaction, the catalyst was removed by filtration to afford 4-(2-morpholin-4-ethyl)aniline (1.9 g, quantitative yield) as a white solid. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 6.99 (d, J=9Hz, 2H), 6.62 (d, J=9Hz, 2H), 3.73 (m, 4H), 3.60 (brs, 2H), 2.70-2.65 (m, 2H), 2.54-2.47 (m, 6H).
[1] Angewandte Chemie, International Edition, 2012, vol. 51, # 42, p. 10500 - 10504,5
[2] Angewandte Chemie, 2012, vol. 124, # 42, p. 10652 - 10656,5
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 42, p. 10500 - 10504
[4] Angew. Chem., 2012, vol. 124, # 42, p. 10652 - 10656,5
[5] Patent: WO2013/43232, 2013, A2. Location in patent: Paragraph 00600
