4-(Morpholinomethyl)benzylamine

Synthesis

37812-51-4

91271-84-0

General procedure for the synthesis of 4-(morpholinomethyl)benzylamine: lithium aluminum hydride (1.13 g, 29.7 mmol) was slowly added to tetrahydrofuran (THF, 50 mL) at 0 °C under nitrogen protection, followed by the dropwise addition of 4-(morpholin-4-ylmethyl)benzyl nitrile (2 g, 9.89 mmol) in THF solution (10 mL). The reaction mixture was stirred at 0 °C for 1 h and then brought to room temperature and continued to stir overnight. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched by the slow addition of water (1.15 mL). Next, ether (125 mL) and 3N NaOH aqueous solution (1.15 mL) were added followed by water (3.45 mL) and stirred for 1 hour at room temperature. The solid residue was removed by filtration and the filtrate was concentrated in vacuum to give 4-(morpholinomethyl)benzylamine as a colorless oil (1.87 g, 94% yield). Mass spectrum (APCI+) m/z: 207 ([M + H]+).

References