1-(2-Hydroxyethyl)piperazine → HCID 22272640, compound

HRID 1064876Notes

Reaction equation

HRID 1064876 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[C:8]([F:15])[C:7]=1[CH:16]([CH3:18])[CH3:17])=[O:4].[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:2][C:3]([NH:5][C:6]2[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[C:8]([F:15])[C:7]=2[CH:16]([CH3:18])[CH3:17])=[O:4])[CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 22272849HCID 22272849, compound

Product 1

HCID 22272640HCID 22272640, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of this acetamide (498 mg, 1.57 mmol) in acetonitrile (10 ml) were added 1-(2-hydroxyethyl)piperazine (371 mg, 2.85 mmol) and potassium carbonate (469 mg, 3.39 mmol) successively with ice-cooling, and stirred at room temperature for 12 hours. The reaction solution was diluted with water and extracted with chloroform. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting reside was purified by a silica gel column chromatography (silica gel 50 g, developing solvent; chloroform:methanol=25:1 10:1) and recrystallized from ether-hexane to provide 575 mg (yield 99%) of 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-(2,6-diisopropyl-3-fluorophenyl)acetamide as colorless needles.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting reside was purified by a silica gel column chromatography (silica gel 50 g, developing solvent; chloroform:methanol=25:1 10:1)
  7. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-a5c2c13b317c4c1daef7bdc3775c4faf
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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