Benzoyl chloride → N-[4-(4-Benzoyl-piperazine-1-sulfonyl)-phenyl]-acrylamide

HRID 1841927Notes

Reaction equation

HRID 1841927 reaction equation
C(N(C(C)C)CC)(C)C.[N:10]1([S:16]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:29])[CH:27]=[CH2:28])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[C:30]([N:13]1[CH2:12][CH2:11][N:10]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([NH:25][C:26](=[O:29])[CH:27]=[CH2:28])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH2:15][CH2:14]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 56953730N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide

Product 1

HCID 67194760N-[4-(4-Benzoyl-piperazine-1-sulfonyl)-phenyl]-acrylamideYield 13.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (0.24 ml, 1.36 mmol) was added in one portion to a stirred solution of N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide (0.1 g, 0.34 mmol) in THF (5 ml). The mixture was stirred at room temperature for 5 minutes before benzoyl chloride (0.05 ml, 0.44 mmol) was added drop wise and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. The crude reaction mixture was concentrated under vacuum and the residue was purified by Prep HPLC to give the title compound (0.018 g, 13% yield) as a white powder.

Workup

  1. additionwas added drop wise
  2. customThe crude reaction mixture
  3. concentrationwas concentrated under vacuum
  4. customthe residue was purified by Prep HPLC

Sources & evidence

ORD record
ord-49ca5b650af8410d9a43bb4f4eabda26
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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