Acetic Acid → HCID 28423879, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, add sodium cyanoborohydride (9.6 g, 152 mmol) to a solution of 4-cyanobenzaldehyde (5 g, 38 mmol), cyclohexylamine (3.8 g, 38 mmol) and acetic acid (0.46 g, 7.6 mmol) in methanol (100 mL) at 0° C. Warm the mixture to room temperature and stir overnight. Add water (100 mL) and adjust the pH to 10 with 3N aqueous NaOH. Extract with DCM and wash the organic phase with water and brine. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (500 g) eluting with hexane/EtOAc (1:0 to 1:1 gradient) to obtain the desired intermediate (6.9 g, 86%). MS (APCI+) m/z: 215 (M+H)+.

Provenance & Evidence