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1-(2-Hydroxyethyl)piperazine → 2-[4-(2-Hydroxyethyl)piperazin-1-yl]-N-[2,4-dibromo-6-methyl-3-pyridyl]acetamide

HRID 348557
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348557
[Br:1][C:2]1[C:7]([NH:8][C:9](=[O:12])[CH2:10]Br)=[C:6]([Br:13])[CH:5]=[C:4]([CH3:14])[N:3]=1.[OH:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[C:7]([NH:8][C:9](=[O:12])[CH2:10][N:21]2[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][OH:15])[CH2:19][CH2:20]2)=[C:6]([Br:13])[CH:5]=[C:4]([CH3:14])[N:3]=1
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Komponenten

5

Edukt 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 10430271N-[2,4-dibromo-6-methylpyridin-3-yl]-2-bromoacetamide

Produkt 1

HCID 116406602-[4-(2-Hydroxyethyl)piperazin-1-yl]-N-[2,4-dibromo-6-methyl-3-pyridyl]acetamideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342Acetonitrile
Lösungsmittel

Versuchsvorschrift

N-[2,4-Dibromo-6-methylpyridin-3-yl]-2-bromoacetamide (1.4 g, 37.3 mmol) was dissolved in acetonitrile (60 mL). 1-(2-Hydroxyethyl)piperazine (0.58 g, 4.48 mmol) was added to the solution with stirring and cooling with ice, and then potassium carbonate (37.5 g, 0.271 mol) was added thereto. The temperature of the mixture was elevated to room temperature, and the mixture was stirred for 24 hours. After completion of reaction, the solvent was removed under reduced pressure. Chloroform and water was added to the residue, and the organic layer was collected from the mixture. The aqueous layer was further extracted with chloroform and the two organic layers were combined together. The combined organic layer was washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (developer: ammonia-saturated methanol/chloroform=1/20), to thereby obtain 1.613 g of N-[2,4-dibromo-6-methylpyridin-3-yl]-2-[4-(2-hydroxyethyl)piperazin-1-yl]acetamide as an amorphous (yield: 99%).

Aufarbeitung

  1. temperaturecooling with ice
  2. customwas elevated to room temperature
  3. stirringthe mixture was stirred for 24 hours
  4. customAfter completion of reaction
  5. customthe solvent was removed under reduced pressure
  6. additionChloroform and water was added to the residue
  7. customthe organic layer was collected from the mixture
  8. extractionThe aqueous layer was further extracted with chloroform
  9. washThe combined organic layer was washed with saturated brine
  10. dry with materialdried over sodium sulfate anhydrate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified through silica gel column chromatography (developer: ammonia-saturated methanol/chloroform=1/20)

Quellen und Nachweise

ORD-Eintrag
ord-4b026e6e1cad481f8a555f17ebac6cdd
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176306B2

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