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

HRID 348557Notes

Reaction equation

HRID 348557 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-4b026e6e1cad481f8a555f17ebac6cdd
Source dataset
uspto-grants-2007_02
Patent number
US07176306B2

Reaction notes

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