[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]#[N:11])[CH2:4]1>[Ni].CCO>[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][NH2:11])[CH2:4]1A mixture of nitrile 282 (3.5 g, 22.7 mmol) and Raney Nickel (50% w/w suspension in water, 8 g) in EtOH (100 mL) and cNH3 (10 mL) was stirred under H2 (60 psi) for 22 h. The mixture was filtered through Celite, the solid washed with EtOH (60 mL) and the solvent evaporated to give diamine 283 as a crude colourless oil (3.48 g, 97%) which was used without further purification: HRMS (FAB+) calcd for C8H19N2O (MH+) m/z 159.14974, found 159.14976.
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