109-11-5

3-Morpholinone is used as a reactant in the synthesis of 3-Morpholinone derivates. An example of this is 4-(4-Aminophenyl)-3-morpholinone, the key intermediate in the synthesis of Rivaroxaban (an anticoagulant).

To a solution of 2-aminoethanol (197 mmol, 1.1 eq.) in isopropanol (100 mL) was added sodium metal (197 mmol, 1.1 eq.) in batches. The reaction mixture was heated and stirred at 50 °C for 5 h to give a yellow solution, which was subsequently cooled to 0 °C in an ice-water bath. Ethyl chloroacetate (179 mmol, 1.0 eq.) was added slowly and dropwise at 0 °C and the yellow suspension formed was heated and stirred at 80 °C for 2 hours. After completion of the reaction, insoluble impurities were removed by filtration through filter paper and the filtrate was washed with isopropanol. The filtrate and washings were combined and concentrated under reduced pressure to give a brown solid. Finally, the crude product was recrystallized using mixed isopropanol/ethyl acetate solvent to give 3-morpholinone in 52% yield.