Triethylamine → (3,4-Dinitrophenyl)-(4-methylpiperazin-1-yl)methanone

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,4-dinitrobenzoic acid (10.6 g, 50 mmol) and SOCl2 (50 mL) was heated at reflux for 6 hrs. Then the mixture was evaporated to dryness in vacuo. The residue was dissolved in CH2Cl2 (50 mL) and cooled to 5° C. To this solution, N-methylpiperazine (5.5 g, 55 mmol) and Et3N (5.5 g, 55 mmol) were added dropwise as a solution in CH2Cl2 (50 mL). After stirring overnight at rt, the combined organic phase was washed with water (100 mL), dried over Na2SO4, filtered and concentrated, the resulting residue was purified by silica gel chromatography (eluent: 5% MeOH in CH2Cl2) to give a yellow solid (14.0 g, 95.2%). 1H NMR (300 MHz, DMSO-d6) δ: 8.29 (1 H, s), 8.25-8.27 (1 H, d, J=9.0 Hz), 7.95-7.98 (1 H, d, J=9.0 Hz), 3.62 (2 H, m), 3.28 (2 H, m), 2.38 (2 H, m), 2.26 (2 H, m), 2.19 (3 H, s).

Provenance & Evidence