Water → N-[2-(4-benzenesulfonyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide

HRID 1178038Notes

Reaction equation

HRID 1178038 reaction equation
Cl.[O:2]=[C:3]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH2:4][NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>C(Cl)Cl>[C:27]1([S:33]([N:24]2[CH2:23][CH2:22][N:21]([C:3](=[O:2])[CH2:4][NH:5][C:6](=[O:20])[C:7]3[CH:8]=[CH:9][C:10]([O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:11][CH:12]=3)[CH2:26][CH2:25]2)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 66953134N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide hydrochloride

Product 1

HCID 27510202N-[2-(4-benzenesulfonyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamideYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TEA (0.074 mL, 0.53 mmol) was added dropwise to a chilled (0° C.) mixture of N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide hydrochloride (100 mg, 0.27 mmol) in DCM (5 mL). After 5 minutes, benzenesulfonyl chloride (0.032 mL, 0.26 mmol) was added and the resulting mixture was stirred at room temperature for 5 hours. DCM was added, followed by the addition of iced water. The product was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (using silica gel of mesh size of 60-120 and 70:30 EtOAc:hexane as eluent) to afford N-[2-(4-benzenesulfonyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide in 47% yield. LC-MS purity: 98%, 1H NMR (DMSO-D6): δ 8.5 (t, 1H), 7.9 (d, 2H), 7.8 (m, 3H), 7.6 (m, 2H), 7.4 (t, 2H), 7.2 (t, 1H), 7.1 (d, 2H), 7 (d, 2H), 4.1 (d, 2H), 3.6 (m, 4H), 2.9 (m, 4H).

Workup

  1. temperaturea chilled
  2. washThe product was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (using silica gel of mesh size of 60-120 and 70:30 EtOAc:hexane as eluent)

Sources & evidence

ORD record
ord-dc6df5c5578542ca9da7c235d3f7cdd3
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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