Allylamine → Benzyl allylcarbamate

Temperature

-5 °C

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).

1. customInto a 250 mL single neck flask were placed
2. temperatureThe reaction mixture was warmed up to RT
3. extractionThe product was extracted with EtOAc
4. customthe organic layer was separated
5. washwashed twice with H2O
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced vacuum
9. customThe resulting oil was further purified via flash chromatography (Silica gel, isocratic)
10. washeluting with a solvent of Hexanes/EtOAc 20%

ORD record

ord-aebc639531024a29ade75f73f1588c15

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06703425B2