Hydroxyacetonitrile → (4-Methoxy-1-piperidinyl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

4-Methoxypiperidine (286) (10.1 g, 87.6 mmol) was added dropwise to a stirred aqueous solution of glycolonitrile (55%, 10.0 g, 96.4 mmol) at 5° C. and the solution was stirred at 70° C. for 1 h. The solution was cooled, diluted with Et2O (50 mL) and washed with water (2×20 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give nitrile 287 (10.25 g, 76%) as a colourless oil: 1H NMR δ 3.51 (s, 2H, CH2CN), 3.35 (s, 3H, OCH3), 3.21-3.28 (m, 1H, CHO), 2.72-2.78 (m, 2H, CH2N), 2.40-2.46 (m, 2H, CH2N), 1.90-1.98 (m, 2H, CH2N), 1.60-1.69 (m, 2H, CH2).

Provenance & Evidence