Sodium Iodide → 1-Acetyl-4-[2-(4-nitrophenoxy)ethyl]piperazine

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of N-acetylpiperazine (5.10 g, 40.0 mmol) in acetonitrile (100 mL) was added 1-(4-nitrophenoxy)-2-bromoethane (10.0 g, 40.0 mmol), K2CO3 (15 g, 108 mmol), and NaI (0.90 g, 6.0 mmol). The mixture was stirred under nitrogen at 70° C. for 24 hours, cooled, and concentrated. The residue was partitioned between ethyl acetate/10% aqueous K2CO3. The organic phase was dried and concentrated to afford crude product which was purified by flash column chromatography (5% CH3OH/CH2Cl2) to afford 7.07 g (61%) of 1-acetyl-4-[2-(4-nitrophenoxy)ethyl]piperazine as a semisolid: 1H NMR (CDCl3): δ8.20 (d, J=9.6 Hz, 2H), 6.95 (d, J=9.6 Hz, 2h), 4.20 (t, J=6.0 Hz, 2H), 3.65 (m, 2H), 3.50 (m, 2H), 2.85 (t, J=6.0 Hz, 2H), 2.55 (m, 6H), 2.08 (s, 3H).

Provenance & Evidence