Benzyl chloroformate → HCID 18964311, compound

Participants

Reaction Steps

Benzyl chloroformate (15.7 mL, 0.11 mol) was added dropwise to a stirred mixture of N,N-diethyl-p-phenylenediamine hydrochloride (20 g, 0.1 mol) and sodium hydrogen carbonate (42.0 g) in dichloromethane at room temperature under nitrogen. After 16 hours at room temperature, the precipitate which had formed was removed by filtration. The solid residue was washed with dichloromethane and the combined dichloromethane extracts were concentrated to produce a brown oil. This material was purified by preparative high pressure liquid chromatography (hereinafter HPLC) on silica gel eluting with 10% hexanes/dichloromethane followed by dichloromethane alone. The resultant oil was triturated with hexanes to give N-benzyloxycarbonyl-4-diethylaminoaniline (18.25 g, 61% yield) as a crystalline solid. The structure of this compound was confirmed by mass spectroscopy and by 1H NMR spectroscopy.

Provenance & Evidence