N'-(2-methoxyethyl)-N'-methylethane-1,2-diamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of nitrile 267 (3.06 g, 23.4 mmol) and Raney-Nickel (50% slurry in water, 15 g) in EtOH (100 mL) and cNH3 (10 mL) was stirred vigorously under H2 (60 psi) for 5 h. The mixture was filtered through Celite, washed with EtOH (60 mL) and the solvent evaporated, keeping the bath temperature below 35° C. to give crude diamine 268 (Pasini, C.; et al., Farmaco, Edizione Scientifica 1965, 20, 673-685) (2.45 g, 79%) as a colourless oil, which was used without further purification: 1H NMR [(CD3)2SO] δ 3.39 (t, J=6.0 Hz, 2H, CH2O), 3.22 (s, 3H, OCH3), 2.61 (br s, 2H, CH2N), 2.49 (t, J=6.0 Hz, 2H, CH2N), 2.36 (t, J=6.7 Hz, 2H, CH2N), 2.17 (s, 3H, NCH3), NH2 not observed; 13C NMR δ 59.4, 57.9, 56.3, 42.4, 38.6, 20.2. The mixture was filtered through Celite washed with EtOH (60 mL) the solvent evaporated the bath temperature below 35° C.