[(3-Methoxypropyl)(methyl)amino]acetonitrile → (2-Aminoethyl)(3-methoxypropyl)methylamine

Participants

Reaction Steps

A mixture of nitrile 273 (1.94 g, 14.0 mmol), cNH3 (8 mL) and Raney Nickel (50% slurry in water, 5.3 g) in EtOH (100 mL) was stirred under H2 (60 psi) for 4 h. The mixture was filtered through Celite, washed with EtOH (50 mL) and the solvent was evaporated to give crude diamine 274 (1.65 g, 83%) as a yellow oil, which was used without further purification: 1H NMR δ 3.42 (t, J=6.4 Hz, 2H, CH2N), 3.33 (s, 3H, OCH3), 2.76 (t, J=6.1 Hz, 2H, CH2), 2.43 (t, J=7.2 Hz, 2H, CH2), 2.40 (t, J=6.2 Hz, 2H, CH2), 2.21 (s, 3H, NCH3), 1.74 (tt, J=7.2, 6.2 Hz, 2H, CH2), NH2 not observed; MS (APCI) m/z 147 (MH+, 100%); HRMS calcd for C7H18N2O (M+) m/z 146.1419, found 146.1424.

Provenance & Evidence