p-Toluenesulfonic acid → HCID 12569395, compound

Participants

Reaction Conditions

Reaction Steps

p-Toluenesulphonic acid (1.91 g, 10.1 mmol) in THF (10 mL) was treated portionwise with morpholine (1.75 g, 1.76 mL, 20.1 mmol) and 4-pyridinecarbox-aldehyde (1 g, 9.3 mmol) was added with stirring. The reaction mixture was heated at 100° C. for 2 h. After cooling to room temperature potassium cyanide (0.82 g, 12.6 mmol) was added as a slurry in water (1.5 mL) and the reaction mixture heated for 18 h at reflux. After cooling to room temperature the THF was removed in vacuo and the residue extracted with DCM, dried over sodium sulphate, concentrated, dissolved in ethyl acetate, then filtered through a pad of silica eluting with ethyl acetate. The residue was chromatographed on silica in DCM/ethyl acetate (0-100% gradient) to give the title compound (1.5 g). δH (DMSO-d6) 8.68-8.64 (2H, m), 7.49-7.46 (2H, m), 5.53 (1H, s), 3.66-3.60 (4H, m), 2.59-2.51 (2H, m), 2.43-2.35 (2H, m).

Provenance & Evidence