N,N'-Dimethylethylenediamine → 1,4-Dimethyl-3-(4-nitrophenyl)piperazin-2-one

Participants

Reaction Steps

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with N1,N2-dimethylethane-1,2-diamine (1.61 g, 18.2 mmol), ethanol (5 mL) and 2 (500 mg, 1.82 mmol), and the reaction was stirred at room temperature for 1 h. After this time, the reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography to afford an 89% yield (404 mg) of 3 as a yellow oil: 1H NMR (500 MHz, DMSO-d6) δ 8.18 (d, 2H, J=8.5 Hz), 7.60 (d, 2H, J=8.5 Hz), 3.87 (s, 1H), 3.61 (td, 1H, J=12.0, 4.0 Hz), 3.26 (ddd, 1H, J=12.0, 4.0, 2.5 Hz), 3.02 (ddd, 1H, J=12.0, 4.0, 2.5 Hz), 2.84 (s, 3H), 2.64 (td, 1H, J=12.0, 4.0 Hz), 2.06 (s, 3H).

Provenance & Evidence