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

HRID 2245538Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:18]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:21]2[CH2:20][CH2:19][N:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

customThe resulting reaction mixture
stirringto stir for 16 h at room temperature
filtrationthe reaction mixture was filtered
concentrationthe organic solution was concentrated in vacuo
customThe residue was purified an a silica gel column

Sources & evidence

ORD record: ord-25612aaf2e6a4ab5979fcbbe4c2bbdbd
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683067B2

Reaction notes

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