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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 227517
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HRID 227517 반응식
[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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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-33d545491b804cdc99b297dfbd08452e
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560547B2

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