Allylamine → Benzyl allylcarbamate

Participants

Reaction Conditions

Reaction Steps

Into a 250 mL single neck flask were placed allylamine (5 mL, 66.6 mmol) and triethylamine (11.1 mL, 80 mmol) in methylene chloride (80 mL). The mixture was cooled to −5° C. before being treated with benzylchloroformate (10 mL, 70 mmol) gradually. The reaction mixture was warmed up to RT while stirring overnight. The product was extracted with EtOAc and the organic layer was separated and washed twice with H2O, dried over anhydrous Na2SO4, filtered, and concentrated under reduced vacuum. The resulting oil was further purified via flash chromatography (Silica gel, isocratic) and eluting with a solvent of Hexanes/EtOAc 20% to provide the intermediate title compound, (phenylmethoxy)-N-prop-2-enylcarboxamide, (8.7 g, 68%) as oil. Electron spray M.S. 192 (M*+1).

Provenance & Evidence