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Triethylamine → 2-Methyl-4-(4-methylsulfonylpiperazin-1-yl)quinoline

HRID 333932
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333932
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([S:26]([CH3:25])(=[O:28])=[O:27])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 7023182-Methyl-4-(piperazin-1-yl)quinoline

Produkt 1

HCID 668358192-Methyl-4-(4-methylsulfonylpiperazin-1-yl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Methyl-4-piperazin-1-yl-quinoline (227.3 mg, 1 mmol) was dissolved in anhydrous dichloromethane (7 ml), triethylamine was added (209 μl, 1.5 mmol), followed by methanesulfonyl chloride (85 μl, 1.1 mmol) which was added dropwise with ice-cooling. The mixture was diluted with dichloromethane and washed with 5% sodium bicarbonate solution. The wash solution was extracted with dichloromethane, the organic phases were combined and washed with 5% sodium bicarbonate solution, water and dried over magnesium sulfate. After evaporation of the solvent under reduced pressure 265 mg of a white foam were obtained (0.87 mmol, 87%) which was used directly in the next step.

Aufarbeitung

  1. additionwas added dropwise with ice-
  2. temperaturecooling
  3. washwashed with 5% sodium bicarbonate solution
  4. extractionThe wash solution was extracted with dichloromethane
  5. washwashed with 5% sodium bicarbonate solution, water
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation of the solvent under reduced pressure 265 mg of a white foam
  8. customwere obtained (0.87 mmol, 87%) which

Quellen und Nachweise

ORD-Eintrag
ord-15aad25a38c74dffaf66c4beaac41fe2
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883791B2

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