1-(5-Isoquinolinylsulfonyl)piperazine → HCID 13116949, compound

HRID 1248758Notes

Reaction equation

HRID 1248758 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.C(=O)([O-])[O-].[K+].[K+].[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)(Cl)Cl>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([N:14]3[CH2:19][CH2:18][N:17]([C:26](=[O:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:16][CH2:15]3)(=[O:12])=[O:13])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 35451-(5-Isoquinolinylsulfonyl)piperazineHCID 7412Benzoyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 13116949HCID 13116949, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In 50 ml of chloroform were added 2.77 g of 1-(5-isoquinolinesulfonyl)piperazine, i.e., Compound 35 and 1.54 g of anhydrous potassium carbonate, and to the mixture was added dropwise 1.70 g of benzoyl chloride under cooling with ice, and the mixture was stirred at a temperature of 15° C. to 20° C. for three hours. The reaction solution was washed with a 1N aqueous sodium hydroxide solution, then with water and dried with anhydrous magnesium sulfate. After the chloroform was distilled therefrom, the residue thus obtained was subjected to a silica gel column chromatography (silica gel: 70 g; solvent: chloroform) to give 2.7 g of 1-(5-isoquinolinesulfonyl)-4-benzoylpiperazine, i.e., Compound (58) in a yield of 71%.

Workup

  1. temperatureunder cooling with ice
  2. washThe reaction solution was washed with a 1N aqueous sodium hydroxide solution
  3. dry with materialwith water and dried with anhydrous magnesium sulfate
  4. distillationAfter the chloroform was distilled
  5. customthe residue thus obtained

Sources & evidence

ORD record
ord-88af37290cad438cad58d1a473d770f0
Source dataset
uspto-grants-1985_06
Patent number
US04525589

Reaction notes

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