Cesium carbonate → HCID 58425605, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-2-fluoro-1-nitrobenzene (0.6 g, 2.75 mmol) phenol (0.28 g, 3.02 mmol) and cesium carbonate (1.8 g, 5.5 mmol) in NMP (6 mL) was heated at 70° C. for 12 h, cooled then diluted with H2O (15 mL) and extracted with ethyl acetate (3×10 mL). The organics were washed with brine (8 mL), dried (Na2SO4) then filtered and concentrated in vacuo. The colorless solid was dissolved in NMP (2 mL) to which was added phenyl(piperazin-1-yl)methanone (1.0 g, 5.5 mmol) and the solution was heated to 110° C. for 16 h. The mixture was cooled and then diluted with H2O (15 mL) and extracted with ethyl acetate (3×10 mL). The organics were washed with brine (8 mL), dried (Na2SO4) then filtered and concentrated in vacuo. The residue was subjected to silica gel column chromatography (20% ethyl acetate/hexane) to furnish (4-(4-nitro-3-phenoxyphenyl)piperazin-1-yl)(phenyl)methanone (0.72 g, 1.8 mmol) as a yellow gum, 65% yield. 1H NMR (500 MHz, CDCl3) d (ppm) 8.11 (d, J=9.5 Hz, 1H), 7.51-7.47 (m, 5H), 7.39 (t, J=8.0 Hz, 2H), 7.18 (t, J=7.5 Hz, 1H), 7.05 (m, 2H), 6.64 (dd, J=2.5 Hz, 9.5 Hz, 1H), 6.35 (d, J=2.5 Hz, 1H), 4.1-3.1 (m, 8H).+ESI HRMS (calcd for C23H21N3NaO4, M+Na) 426.1430, found 426.1424

Provenance & Evidence