Benzyl chloroformate → Benzyl N-(4-aminobutyl)carbamate

Participants

Reaction Steps

To a solution of 1,4-diaminopentane (25 g, 155 mmol) in 100 mL DMF/H2O (1:1) was added 5N NaOH to adjust the pH to 9. CBZ-Cl (3.7 mL, 26 mmol) was added as one portion and stirred at room temperature for 16 hrs. The reaction was acidified to pH 1.25 and washed with diethyl ether. The pH of the reaction was then adjusted to 9.5 and the reaction extracted with EtOAc. The organic layer was washed with H2O, brine, dried over Na2SO4 and evaporated to give title compound (1.57 g, 30%).

Provenance & Evidence