Acetic Acid → 1-{4-[(3-Nitrophenyl)methyl]piperazin-1-yl}ethan-1-one

Participants

Reaction Steps

3-Nitrobenzaldehyde (2.04 g, 13.5 mmol) was dissolved in 50 ml 1,2-dichloroethane. 1-Acetylpiperazine 1.90 g, 14.9 mmol) and sodium triacetoxyborohydride (3.15 g, 14.9 mmol) were added followed by the addition of 0.100 ml of acetic acid. The reaction was allowed to proceed overnight (18 hours) and was then quenched with half-saturated NaHCO3 (aq). The mixture was extracted 3× with DCM and the organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (eluting with 95:5 DCM/MeOH) to afford 1-acetyl-4-(3-nitrobenzyl)piperazine (5-2). 1H NMR (300 MHz, CDCl3) δ 8.22 (s, 1H), 8.13 (dd, J=1.2, 8.3 Hz, 1H), 7.66 (d, J=7.6 Hz, 1H), 7.50 (t, J=7.9 Hz, 1H), 3.63 (t, J=5.2 Hz, 2H), 3.61 (s, 2H), 3.48 (t, J=4.8 Hz, 2H), 2.44 (m, 4H), 2.08 (s, 3H).

Provenance & Evidence