Piperazine → 1-[4-(Trifluoromethyl)benzyl]piperazine

Participants

Reaction Steps

Synthesized according to General Procedure A: 4-trifluoromethylbenzyl chloride (4{15}, 5 g, 25.7 mmol, 1 equiv.), piperazine (13.3 g, 154.2 mmol, 6 equiv.), THF (56.1 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{15} (3.97 g, 67%) as a light yellow liquid. 1H-NMR (400 MHz, CDCl3): δ 7.52 (d, 2H, J=8.0 Hz), 7.40 (d, 2H, J=8.0 Hz), 3.48 (s, 2H), 2.84 (t, 4H, J=4.8 Hz), 2.36 (br s, 4H), 1.55 (br s, 1H). 13C-NMR (100 MHz, CDCl3): δ 142.4, 129.1 (q, JC-F=32.1 Jz) 129.1 (br), 125.0 (br), 124.1 (q, JC-F=338.0 Hz), 62.9, 54.4, 45.9. 19F-NMR (375 MHz, CDCl3): δ-62.5.

Provenance & Evidence