Piperazine → 1-(4-Methylbenzyl)piperazine

Participants

Reaction Steps

Synthesized according to General Procedure A: 4-methylbenzyl chloride (4{13}, 6.1 mL, 46.2 mmol, 1 equiv.), piperazine (23.9 g, 277.4 mmol, 6 equiv.), THF (100.9 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{13} (6.56 g, 96%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 7.18 (d, 2H, J=8.0 Hz), 7.09 (d, 2H, J=7.5 Hz), 3.42 (s, 2H), 2.84 (t, 4H, J=5.0 Hz), 2.37 (br s, 4H), 2.31 (s, 3H), 1.54 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 136.3, 134.7, 129.0, 128.6, 63.2, 54.3, 45.9, 20.9.

Provenance & Evidence