1-(2-Hydroxyethyl)piperazine → HCID 22272790, compound

HRID 1064823Notes

Reaction equation

HRID 1064823 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Br[CH2:17][C:18]([NH:20][C:21]1[C:26]([CH:27]([CH3:29])[CH3:28])=[CH:25][C:24]([OH:30])=[CH:23][C:22]=1[CH:31]([CH3:33])[CH3:32])=[O:19]>C(#N)C.O>[OH:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH2:17][C:18]([NH:20][C:21]2[C:26]([CH:27]([CH3:29])[CH3:28])=[CH:25][C:24]([OH:30])=[CH:23][C:22]=2[CH:31]([CH3:33])[CH3:32])=[O:19])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 99666052-Bromo-N-[4-hydroxy-2,6-bis(1-methylethyl)phenyl]acetamide

Product 1

HCID 22272790HCID 22272790, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (1.52 g, 11 mmol) was added to a solution of 1-(2-hydroxyethyl)piperazine (1.43 g, 11 mmol) and 2-bromo-N-(2,6-diisopropyl-4-hydroxyphenyl)acetamide in acetonitrile (50 ml) and the mixture was stirred at room temperature for 12 hours. The reaction solution was diluted with water and extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively and dried oven anhydrous sodium sulfate and the solvent was evaporated therefrom. The crude crystals were recrystallized from acetone-hexane to provide 2.5 g (yield 69%) of 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-(2,6-diisopropyl-4-hydroxyphenyl)acetamide as colorless needles.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively and dried oven anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe crude crystals were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-2d863b5d35404432b005623641e6391b
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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