Chloroform → 1-(5-Isoquinolinesulfonyl)-2,5-dimethylpiperazine

HRID 638378

Reaction equation

HRID 638378 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH:5]([CH3:8])[CH2:4][NH:3]1.C(N(CC)CC)C.[CH:16]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[C:20]=2[CH:19]=[CH:18][N:17]=1.C(Cl)(Cl)Cl>C(Cl)Cl>[CH:16]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([S:26]([N:3]3[CH2:4][CH:5]([CH3:8])[NH:6][CH2:7][CH:2]3[CH3:1])(=[O:28])=[O:27])[C:20]=2[CH:19]=[CH:18][N:17]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 78162,5-DimethylpiperazineHCID 8471TriethylamineHCID 33716555-Isoquinolinesulfonyl chloride

Product 1

HCID 132291781-(5-Isoquinolinesulfonyl)-2,5-dimethylpiperazineYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In 30 ml of methylene chloride were dissolved 1.75 g of 2,5-dimethylpiperazine and 1.53 g of triethylamine, and to the solution was added dropwise 20 ml of a methylene chloride solution containing 1.73 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the methylene chloride solution, the mixed solution obtained was stirred at a temperature of 5° C. to 10° C. for three hours, and then the reaction mixture solution was washed with water and dried with anhydrous magnesium sulfate. After the methylene chloride was distilled therefrom, the residue obtained was subjected to an alumina column chromatography (alumina: 50 g; solvent: chloroform) to give 1.38 g of 1-(5-isoquinolinesulfonyl)-2,5-dimethylpiperazine, Compound (40) in a yield of 59%.

Workup

  1. temperatureunder cooling with ice
  2. customthe mixed solution obtained
  3. washthe reaction mixture solution was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationAfter the methylene chloride was distilled
  6. customthe residue obtained

Sources & evidence

ORD record
ord-7bd55402f86b43b0b6c675fd34f2c672
Source dataset
uspto-grants-1985_12
Patent number
US04560755

Linked notes

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