4-Morpholinoaniline

10389-51-2

2524-67-6

The general procedure for the synthesis of 4-(4-morpholinyl)aniline from 4-(4-nitrophenyl)morpholine was as follows: referring to the method of Example 20, 4-(4-nitrophenyl)morpholine (10.3 g, 49.5 mmol; purchased from Lancaster Synthesis) was suspended in methanol (130 mL) and a methanolic solution of 2 M ammonia (70 mL). 1 mL of water and 5% palladium carbon catalyst (100 mg) were added. The mixture was placed in a Paar hydrogenation unit and hydrogenated at 50 psi hydrogen pressure for 1 hour. Upon completion of the reaction, the reaction mixture was allowed to cool to room temperature, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by solvent recrystallization from a mixture of ethyl acetate/hexane to give 4-(4-morpholinyl)aniline as a light purple solid (6.2 g, 70% yield, melting point 132-133 °C). The product was analyzed by GC/MS (EI, M+) and showed a molecular ion peak m/z=178.