Piperazine → 1-[[4-(Trifluoromethoxy)phenyl]methyl]piperazine

Participants

Reaction Steps

Synthesized according to General Procedure A: 4-trifluoromethoxybenzyl bromide (4{17}, 5 g, 19.6 mmol, 1 equiv.), piperazine (10.1 g, 117.6 mmol, 6 equiv.), THF (42.8 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{17} (4.75 g, 93%) as a yellow liquid. 1H-NMR (500 MHz, CDCl3): δ 7.28 (d, 2H, J=8.0 Hz), 7.08 (d, 2H, J=8.0 Hz), 3.40 (s, 2H), 2.81 (t, 4H, J=5.0 Hz), 2.33 (br s, 4H), 1.51 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 148.0, 136.9, 130.1, 120.5, 120.3 (q, JC-F=255.5 Hz), 62.6, 54.3, 45.9. 19F-NMR (375 MHz, CDCl3): −58.4.

Provenance & Evidence