Chloroacetyl chloride → Tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate

Participants

Reaction Steps

The above-prepared tert-butyl piperazine-1-carboxylate (500 mg, 2.68 mmol) was treated with chloroacetyl chloride (360 mg, 2.95 mmol) in the presence of DIEA (1.04 g, 8.05 mmol) to give tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate (571 mg, 81% yield) after purification by flash chromatography on a silica gel column (hexane/EtOAc=1:2). C11H19ClN2O3; white solid; mp 68-70° C.; 1H NMR (400 MHz, CDCl3) δ 4.06 (2H, s), 3.58 (2H, m), 3.49 (4H, s), 3.44 (2H, m) 1.47 (9H, s); 13C NMR (100 MHz, CDCl3) δ 164.5, 153.7, 80.2, 46.2, 43.3 (2×), 42.1, 40.9, 28.5; ESI-HRMS calcd for C11H20ClN2O3: 285.0982. found: m/z 285.0985 [M+H]+.

Provenance & Evidence