2-Chloroethanol → 2-(4-(4-Iodophenyl)piperazin-1-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(4-iodophenyl)piperazine (2.25 g, 7.8 mmol) and iPr2NEt (3.4 mL, 19.5 mmol, 2.5 equiv.) in CH3CN was added 2-chloroethanol (995 mg, 11.7 mmol, 1.5 equiv.). The resulting mixture was refluxed 7 h (oil temp. 91° C.), then O/N (15 h, oil temp. 83° C.) and 6 h (oil temp. 90° C.) before cooling to rt. After diluting with H2O (30 mL) and sat. NaHCO3 (30 mL), it was extracted with EtOAc (60 mL×2) and washed with H2O and brine. Removal of solvents followed by trituration with MeOH (15 mL) afforded the title compound as a beige solid (1.340 g, 81%). A second trituration of the concentrated mother liquor gave additional 602 mg of crude product as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ 7.46 (d, J=8.4 Hz, 2H), 6.76 (d, J=8.8 Hz, 2H), 4.43 (t, J=5.0 Hz, 1H), 3.51 (q, J=5.6 Hz, 2H), 3.12-3.07 (m, 4H), 2.55-2.49 (m, 4H, partially overlapping with DMSO signal), 2.41 (t, J=6.0 Hz, 2H); MS ESI 332.9 [M+H]+, calcd. for [C12H17IN2O+H]+ 333.0.

Provenance & Evidence