Triethylamine → HCID 10823223, compound

Participants

Reaction Steps

To a solution of 4-(aminomethyl)pyridine (10.7 g, 98.5 mmol) in CH2Cl2 (245 mL) at 0°, was added Et3N (14.2 mL, 19.9 g, 197 mmol) followed by dropwise addition of phenylchloroformate (14.8 mL, 18.5 g, 118 mmol). After stirring for 1 h, the resulting mixture was diluted with EtOAc (1.5 L), the organic phase was washed twice with water and brine, dried over sodium sulfate and concentrated under vacuum. Chromatography (SiO2, gradient EtOAc to 10% MeOH/CHCl3) gave a yellow solid which was recrystallized from EtOAc:hexane (2:1), to yield the desired compound (9.55 g, 41.85 mmol, 42% yield).

Provenance & Evidence