(4-BENZYL-1,4-OXAZINAN-2-YL)METHYLAMINE

110859-48-8

110859-47-7

General procedure for the synthesis of (4-benzyl-2-morpholinyl)methanamine from 2-[[4-(benzyl)-2-morpholinyl]methyl]-1H-isoindole-1,3(2H)-dione: To a 50 mL single-necked round-bottomed flask was added 2-(4-benzylmorpholin-2-yl)methylphthalimide (1.3 g, 3.87 mmol) and hydrazine hydrate (0.38 g, 7.6 mmol) and ethanol (13 mL) was added. The mixture was heated to 80 °C and then stirred for 4 hours. After completion of the reaction, which was monitored by thin layer chromatography (TLC), the resulting solution was cooled to room temperature and filtered to separate the inorganic material. The filtrate was concentrated under vacuum, 10% sodium hydroxide solution (10 mL) was added and extracted twice with dichloromethane (20 mL). All extracted organic layers were combined, dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under vacuum to give a solid product. The resulting solid was dried in an oven at 60 °C to give (4-benzylmorpholin-2-yl)methylamine (550 mg, 69% yield). The dried product was used directly in the subsequent reaction.