2-(azepan-1-yl)acetonitrile

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

Procedure: A mixture of nitrile 290 (5.58 g, 40.4 mmol) and Raney Nickel (50% w/w in water, ca. 5 mL) in EtOH (50 mL) and cNH3 (4 mL) was stirred under H2 (60 psi) for 16 h. The mixture was filtered through Celite, washed with EtOH (3×10 mL) and the solvent evaporated to give crude diamine 291 as an oil (2.03 g, 35%) which was used without further purification: 1H NMR δ 2.72 (t, J=6.1 Hz, 2H, CH2N), 2.60-2.68 (m, 4H, 2×CH2N), 2.53 (t, J=6.1 Hz, 2H, CH2N), 1.55-1.66 (m, 10H, 4×CH2, NH2). The mixture was filtered through Celite washed with EtOH (3×10 mL) the solvent evaporated

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Azepane (289) (4.9 mL, 43.8 mmol) was added dropwise to a stirred aqueous solution of glycolonitrile (55%, 5.0 g, 48.2 mmol) at 5° C. and the solution was stirred at 70° C. for 30 min. The solution was cooled, diluted with water (20 mL), washed with Et2O (3×50 mL). The organic fraction was dried and the solvent evaporated to give nitrile 290 (5.58 g, 92%) as a colourless oil: 1H NMR δ 3.56 (s, 2H, CH2CN), 2.71 (br dd, J=5.8, 5.5 Hz, 4H, 2×CH2N), 1.67-1.73 (m, 4H, 2×CH2), 1.59-1.64 (m, 4H, 2×CH2). The solution was cooled washed with Et2O (3×50 mL) The organic fraction was dried the solvent evaporated