Hydrochloric Acid → Benzyl N-(2-aminoethyl)carbamate hydrochloride

Participants

Reaction Steps

N,N-Bis-Carbobenzyloxyethylenediamine 11 (23.91 g, 72.8 mmol) in glacial acetic acid (100 mL) was treated with 12M HCl (12.1 mL, 2 equiv). The stirred mixture was heated at reflux for 1 h and then left to stand at rt overnight. A small amount of solid was removed by filtration and the filtrate was diluted with ether (700 mL) and left to stand at rt for 2 h. The resulting white solid product was collected by filtration, washed repeatedly with ether, and dried in a vacuum dessicator overnight (9.2440 g, 55%). 1H-NMR (DMSO-d6) δ 2.87 (t, 2H), 3.30 (q, 2H), 5.04 (s, 2H), 7.33 (m, 5H), 7.49 (brt, 1H), 8.22 (br, 3H).

Provenance & Evidence