p-Toluenesulfonic acid → HCID 14493457, compound

Participants

Reaction Steps

To 3-cyanobenzaldehyde (8.0 g, 61.0 mmol) was added morpholine (10.63 g, 122.0 mmol), p-toluenesulfonic acid (12.18 g, 64.05 mmol), and then a solution of potassium cyanide (3.97 g, 61.0 mmol) in 12mL water. The mixture was refluxed for 75 minutes then cooled to room temperature and partitioned between satd. sodium bicarbonate and methylene chloride. The aqueous portion was extracted with methylene chloride (1×), and the resulting organic portion washed with satd. sodium bisulfite (1×). The organic portion was dried over sodium sulfate and concentrated in vacuo. Crystallization from hot ethanol gave 3-[cyano(morpholin-4-yl)methyl]benzonitrile (11.83 g, 85%). LRMS m/z (M+H) Calcd: 228.3, found: 228.1.

Provenance & Evidence