1-(5-Isoquinolinylsulfonyl)piperazine → HCID 13116945, Verbindung

HRID 638377

Reaktionsgleichung

Reaktionsgleichung von HRID 638377
[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.[OH-].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[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]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:16][CH2:15]3)(=[O:12])=[O:13])[C:5]=2[CH:4]=[CH:3][N:2]=1

Komponenten

5

Edukt 3

HCID 35451-(5-Isoquinolinylsulfonyl)piperazineHCID 7503Benzyl ChlorideHCID 14797Potassium Hydroxide

Produkt 1

HCID 13116945HCID 13116945, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 150 ml of ethanol were added 2.77 g of 1-(5-isoquinolinesulfonyl)piperazine, i.e., Compound (35), 1.0 g of potassium hydroxide and 1.9 g of benzyl chloride, and the mixture was refluxed under heating for five hours. After the ethanol was removed from the reaction solution, 100 ml of chloroform was added to the resulting solution, and the solution obtained was washed with a buffer solution having a pH of 5.5 and extracted twice with 20 ml of a 2N aqueous hydrochloric acid solution. The aqueous hydrochloric acid layer was rendered alkaline, extracted twice with 50 ml of chloroform, and the chloroform layer extracted was washed with water and dried with anhydrous magnesium sulfate. After the chloroform was distilled therefrom under reduced pressure, 5 ml of a 10N aqueous hydrochloric acid solution was added to the residue and the mixture was condensed to dryness. The crystalline residue thus obtained was recrystallized from ethanol to give 2.9 g of 1-(5-isoquinolinesulfonyl)-4-benzylpiperazine [i.e., Compound (56)] dihydrochloride in a yield of 66%.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for five hours
  3. customAfter the ethanol was removed from the reaction solution, 100 ml of chloroform
  4. additionwas added to the resulting solution
  5. customthe solution obtained
  6. washwas washed with a buffer solution
  7. extractionextracted twice with 20 ml of a 2N aqueous hydrochloric acid solution
  8. extractionextracted twice with 50 ml of chloroform
  9. extractionthe chloroform layer extracted
  10. washwas washed with water
  11. dry with materialdried with anhydrous magnesium sulfate
  12. distillationAfter the chloroform was distilled
  13. additionunder reduced pressure, 5 ml of a 10N aqueous hydrochloric acid solution was added to the residue
  14. customcondensed to dryness
  15. customThe crystalline residue thus obtained
  16. customwas recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d802405c32be480bb2ba6396cc855b8b
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560755

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