Potassium Carbonate → Tert-butyl 4-(6-chloropyridin-3-ylsulfonyl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

6-Chloropyridine-3-sulfonyl chloride (0.318 g, 1.5 mmol; described in: Naegeli, C. et al. Helv. Chim. Acta. 1938, 21, 1746-1750) was added to a suspension of potassium carbonate (0.276 g, 2.0 mmol) in dichloromethane (3 mL) at room temperature. The mixture was stirred for 5 min at 0° C. followed by the addition of tert-butyl 1-piperazinecarboxylate (0.363 g, 2.0 mmol). The resulting reaction mixture was allowed to stir for 16 h at room temperature and the reaction mixture was filtered and the organic solution was concentrated in vacuo. The residue was purified an a silica gel column using heptane/ethyl acetate, (2:1), as the eluent to afford 0.188 g (35% yield) of the title compound as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.74 (d, J=2.0 Hz, 1H), 7.96 (dd, J=8.4, 2.8 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 3.53 (t, J=5.2 Hz, 4H), 3.03 (t, J=5.2 Hz, 4H), 1.42 (s, 9H); MS (EI) m/z 362 (M++1).

Provenance & Evidence