Piperazine → HCID 86681345, compound

Participants

Reaction Steps

Synthesized according to General Procedure A: 3,4-bis(benzyloxy)benzyl chloride (4{10}, 2 g, 5.90 mmol, 1 equiv.), piperazine (3.05 g, 35.4 mmol, 6 equiv.), THF (28 mL). Purification with flash column chromatography on silica gel (gradient, 4:1 to 1:4 EtOAc:MeOH) afforded 5{10} (2.12 g, 92%) as a beige solid. 1H-NMR (500 MHz, CDCl3): δ 7.46 (d, 4H, J=7.5 Hz), 7.38-7.34 (m, 4H) 7.32-7.28 (m, 2H), 6.96 (d, 1H, J=2.0 Hz), 6.88 (d, 1H, J=8.0 Hz), 6.80 (dd, 1H, J=2.0, 8.0 Hz), 5.18 (s, 2H), 5.15 (s, 2H), 3.38 (s, 2H), 2.84 (t, 4H, J=5.0 Hz), 2.33 (br s, 4H), 1.74 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 148.5, 147.9, 137.4, 137.3, 131.3, 128.4, 128.3, 127.6, 127.6, 127.3, 127.2, 122.0, 116.1, 114.6, 71.3, 71.1, 63.1, 54.3, 46.0.

Provenance & Evidence