4-Morpholinobenzonitrile → 4-Morpholinobenzylamine

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Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-morpholinobenzonitrile (200 mg, 1.06 mmol, 1.00 equiv) in tetrahydrofuran (10 mL), and LiAlH4 (400 mg, 10.53 mmol, 10.00 equiv). The resulting solution was stirred for 3 h at 60° C. The reaction was then quenched with 1 N NaOH. The solids were removed by filtration. The resulting solution was extracted with 3×20 mL of dichloromethane and the organic layers combined, dried over NaSO4, and concentrated under vacuum. The product was obtained as 120 mg (58%) of a yellow solid. 1H-NMR (300 MHz, CDCl3, ppm): δ 7.26 (m, 2H). 6.91 (m, 2H), 3.87 (m, 6H), 3.16 (m, 4H).

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