p-Fluoronitrobenzene → cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazine

Participants

Reaction Steps

1-Fluoro-4-nitrobenzene (10 g, 70.87 mmol) and (2R,6S)-2,6-dimethylpiperazine (17 g, 148.83 mmol) were heated in acetonitrile (25 ml) at 70° C. for 2 h. The solution was concentrated in vacuo, then the residue was partitioned between DCM and water+sat. sodium hydrogen carbonate. The organic extract was washed with water (4 times), brine, dried and concentrated to give the title compound as a yellow solid which was dried in vac oven overnight at 50° C. (16.13 g, 97%). NMR (400 MHz) 1.04 (d, 6H), 2.39 (m, 2H), 2.77 (m, 2H), 3.89 (dd, 2H), 7.02 (d, 2H), 8.03 (d, 2H); m/z 236.

Provenance & Evidence