Potassium Carbonate → HCID 22272818, compound

HRID 1064849Notes

Reaction equation

HRID 1064849 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([NH:21][C:22]1[C:27]([CH:28]([CH3:30])[CH3:29])=[CH:26][C:25]([OH:31])=[CH:24][C:23]=1[CH:32]([CH3:34])[CH3:33])=[O:20].[Cl-].[NH4+]>C(#N)C>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:18][C:19]([NH:21][C:22]2[C:27]([CH:28]([CH3:30])[CH3:29])=[CH:26][C:25]([OH:31])=[CH:24][C:23]=2[CH:32]([CH3:34])[CH3:33])=[O:20])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 79207Piperazin-1-ylpropanolHCID 99666052-Bromo-N-[4-hydroxy-2,6-bis(1-methylethyl)phenyl]acetamide

Product 1

HCID 22272818HCID 22272818, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(3-hydroxypropyl)piperazine (700 mg, 4.88 mmol) in acetonitrile (15 ml) were added potassium carbonate (805 mg, 5.82 mmol) and 2-bromo-N-(2,6-diisopropyl-4-hydroxyphenyl)acetamide (1.53 g, 4.88 mmol), and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added a saturated ammonium chloride solution and the mixture was extracted with chloroform-methanol mixture solvent. The organic layer was washed with water and a saturated sodium chloride successively and dried over anhydrous sodium sulfate, and the solvent was evaporated therefrom. The resulting residue was recrystallized from chloroform-methanol-hexane to provide 1.13 g (yield 62%) of 2-[4-(3-hydroxypropyl)piperazin-1-yl]-N-[2,6-diisopropyl-4-hydroxyphenyl]acetamide as colorless powdery crystals.

Workup

  1. extractionthe mixture was extracted with chloroform-methanol mixture solvent
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride successively and dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe resulting residue was recrystallized from chloroform-methanol-hexane

Sources & evidence

ORD record
ord-1cfdeda199fb45ea91c8bc5dfd3e1ee0
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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