1-Methylpiperazine → 1-methyl-4-(2-nitrophenyl)piperazine

Participants

Reaction Steps

In a round bottom flask fitted with a condensor and addition funnel, N-methylpiperazine (10.0 grams, 0.1 mol) was stirred while 2-fluoronitrobenzene (14.1 grams, 0.1 mol) was added dropwise under nitrogen. Caution—a vigorous exotherm occurred when approximately 20% of the 2-fluoronitrobenzene had been added. Following completion of the addition (˜30 min.) the reaction was stirred another 60 min. at room temperature, diluted with methylene chloride (100 mL) and washed with saturated aqueous Na2CO3 and saturated aqueous sodium chloride. After drying with MgSO4, the solvent was removed in vacuo to give 2-(4-methylpiperazin-1-yl)-1-nitrobenzene as an orange oil, 20.4 grams. Mass spectrum: 221 (M+), 174 (M-HNO2). 1H-NMR (CDCl3, 300 MHz) δ7.8-7.0 (4H, m), 3.05 (4H, m), 2.55 (4H, t), 2.3 (3H, s).

Provenance & Evidence