Potassium Carbonate → HCID 54159860, compound

Participants

Reaction Steps

A stirred mixture of 0.70 g (0.0025 mole) of 7-fluoro-2H-1,4-benzoxazin-3(4H)-one-6-yl 1-pyrrolidinecarboxylate, 0.60 g (0.0036 mole) of 1-iodopropane, 1.1 g (0.0076 mole) of potassium carbonate, and 0.1 g (0.00038 mole) of 18-crown-6 in 50 mL of acetone was heated at reflux for five hours. The reaction mixture was cooled, filtered and the filtrate evaporated under reduced pressure leaving a residue. The residue was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure leaving a residue. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate-heptane (50:50), to yield 0.6 g of (7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-one-6-yl) 1-pyrrolidinecarboxylate as a solid 73°-75° C., Compound 4 of Table 1. The nmr ir spectra were consistent with the proposed structure.

Provenance & Evidence