Hydroxyacetonitrile → Hexahydro-1H-azepine-1-acetonitrile

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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).

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