2-(3-Methoxyazetidin-1-yl)acetonitrile → 2-(3-Methoxyazetidin-1-yl)ethan-1-amine

Participants

Reaction Steps

A mixture of nitrile 276 (1.76 g, 14.0 mmol), cNH3 (7 mL) and Raney Nickel (50% slurry in water, 4.6 g) in EtOH (100 mL) was stirred under H2 (60 psi) for 5 h. The mixture was filtered through Celite, washed with EtOH (50 mL) and the solvent was evaporated to give crude diamine 277 (950 mg, 52%) as a yellow oil, which was used without further purification: 1H NMR δ 4.03 (p, J=5.8 Hz, 1H, CHO), 3.58-3.63 (m, 2H, CH2N), 3.25 (s, 3H, OCH3), 2.88-2.93 (m, 2H, CH2N), 2.67 (t, J=6.0 Hz, 2H, CH2N), 2.52 (t, J=6.0 Hz, 2H, CH2N), NH2 not observed; MS (APCI) m/z 131 (MH+, 100%); HRMS (FAB+) calcd for C6H15N2O (MH+) m/z 131.1184, found 131.1183.

Provenance & Evidence