Cesium carbonate → HCID 66863894, compound

Participants

Reaction Steps

A mixture of 5-chloro-2-nitrophenylamine (3.000 g, 17.38 mmol), piperazin-1-yl-(2-trifluoromethylphenyl)methanone (5.360 g, 20.80 mmol) and cesium carbonate (11.32 g, 34.76 mmol) was heated at 140° C. in anhydrous DMSO (15 mL) for 12 h. The mixture was cooled and poured over ice water. The solid product obtained was extracted with ethyl acetate. The organic extracts were combined, dried over anhydrous sodium sulphate, concentrated in vacuo. The residue was purified by column chromatography to obtain the product, [4-(3-amino-4-nitrophenyl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone, in 79% yield (6.800 g). 1H NMR (300 MHz, CDCl3) δ 8.01 (d, 1H, J=9.6 Hz), 7.72 (d, 1H, J=7.9 Hz), 7.62 (t, 1H, J=7.1 Hz), 7.54 (t, 1H, J=7.4 Hz), 7.34 (d, 1H, J=7.3 Hz), 6.22 (dd, 1H, J=2.6,9.7 Hz), 6.15 (br. s, 2H), 5.94 (d, 1H, J=2.6 Hz), 4.05-3.93 (m, 1H), 3.90-3.80 (m, 1H), 3.50-3.40 (m, 2H), 3.35-3.20 (m, 4H). MS (ES+) m/z 395.1 (M+1).

Provenance & Evidence