1-(2-Hydroxyethyl)piperazine → HCID 22272726, compound

HRID 1064796Notes

Reaction equation

HRID 1064796 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10].[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(#N)C>[CH2:12]([NH:11][C:9](=[O:10])[CH2:8][N:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][OH:19])[CH2:23][CH2:24]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 2255522-bromo-n-heptylacetamide

Product 1

HCID 22272726HCID 22272726, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (1.52 g, 11 mmol) was added to a solution of this amide (2.36 g, 10 mmol) and 1-(2-hydroxyethyl)piperazine (1.30 g, 10 mmol) in acetonitrile (40 ml) and the mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated and the residue was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate and the residue obtained by evaporation of the solvent was purified by a silica gel column chromatography (75 g of silica gel; developing solvent, ammonia-saturated methanol:chloroform=1:20) to provide 2.39 g (yield 83%) of N-heptyl-2-[4-(2-hydroxyethyl)piperazin-1-yl]acetamide as colorless oil.

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution successively and dried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation of the solvent
  6. customwas purified by a silica gel column chromatography (75 g of silica gel; developing solvent, ammonia-saturated methanol:chloroform=1:20)

Sources & evidence

ORD record
ord-84474e5b0f764304afacb15cea323a13
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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