Acryloyl chloride → 4-(4-Acryloylamino-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1841922Notes

Reaction equation

HRID 1841922 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:33](Cl)(=[O:36])[CH:34]=[CH2:35]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:33](=[O:36])[CH:34]=[CH2:35])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 10617209tert-Butyl 4-(4-aminophenylsulfonyl)piperazine-1-carboxylate

Product 1

HCID 529395194-(4-Acryloylamino-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl esterYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Amino-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (7.1 g, 21 mmol) was dissolved in DCM (70 ml). To this was added diisopropylethylamine (7.3 ml, 42 mmol) in one portion followed by the drop wise addition of acryloyl chloride (1.54 ml, 19 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. The THF was removed under vacuum and the resulting crude material was purified by column chromatography (elution: 60% heptane, 40% ethyl acetate) to give the title compound (5.3 g, 20% yield) as a pale yellow powder.

Workup

  1. customThe THF was removed under vacuum
  2. customthe resulting crude material was purified by column chromatography (elution: 60% heptane, 40% ethyl acetate)

Sources & evidence

ORD record
ord-27a4f291d58e4037a484ff79237d1a0b
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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