4-Aminopyridine → Benzyl carbamate

Participants

Reaction Steps

To a solution of 4-aminopyridine (2.00 g, 21.2 mmol) in CH2Cl2 (30 mL) at 0° C. was added triethylamine (3.50 mL, 25.0 mmol) and benzyl chloroformate (3.10 mL, 22.0 mmol). The ice bath was removed and the resulting mixture was allowed to warm to rt overnight before being poured into saturated aqueous NaHCO3. The product was extracted with CH2Cl2, dried (Na2SO4) and concentrated. The crude product was recrystallized from EtOAc to give 2.90 g (60% yield) of pure benzyl carbamate.

Provenance & Evidence