Acetic Acid → 1-(4-Iodophenyl)-4-isopropylpiperazine

Participants

Reaction Steps

To a mixture of 1-(4-iodophenyl)piperazine (1.44 g, 5 mmol) and acetone (1.47 mL, 20 mmol) in DCE/THF (45 mL/15 mL) was added NaBH(OAc)3 (1.38 g, 6.5 mmol), followed by AcOH (0.5 mL). After addition, the resulting mixture was stirred O/N at rt. The reaction as quenched with sat. NaHCO3 (10 mL) and H2O (20 mL), and was then extracted with EtOAc (2×60 mL), dried over MgSO4 and concentrated to give the crude title compound as a light yellow solid (1.396 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ 7.46 (d, J=8.4 Hz, 2H), 6.75 (d, J=8.8 Hz, 2H), 3.12-3.07 (m, 4H), 2.65 (p, J=6.5 Hz, 1H), 2.56-2.52 (m, 4H), 0.98 (d, J=6.4 Hz, 6H); MS ESI 330.9 [M+H]+, calcd. for [C13H19IN2+H]+ 331.1.

Provenance & Evidence