Piperazine → 1-((2-Chloro-6-fluorophenyl)methyl)piperazine

Participants

Reaction Steps

Synthesized according to General Procedure A: 2-chloro-6-fluorobenzyl chloride (4{7}, 5 mL, 39.1 mmol, 1 equiv.), piperazine (20.2 g, 234.8 mmol, 6 equiv.), THF (85.4 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{7} (6.92 g, 77%) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 7.14-7.08 (m, 2H), 6.94-6.86 (m, 1H), 3.62 (d, 2H, J=2.0 Hz), 2.78 (t, 4H, J=4.8 Hz), 2.44 (br s, 4H), 1.40 (br s, 1H). 13C-NMR (100 MHz, CDCl3): δ 161.8 (d, JC-F=247.5 Hz), 136.4 (d, JC-F=6.0 Hz), 128.8 (d, JC-F=9.6 Hz), 125.2, 123.6 (d, JC-F=18.0 Hz), 113.7 (d, JC-F=23.3 Hz), 54.0, 52.8, 45.9.

Provenance & Evidence