Potassium Carbonate → HCID 22272678, compound

HRID 1064797Notes

Reaction equation

HRID 1064797 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][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(#N)C>[CH2:12]([NH:11][C:9](=[O:10])[CH2:8][N:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][CH2:20][OH:19])[CH2:24][CH2:25]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79207Piperazin-1-ylpropanolHCID 2255522-bromo-n-heptylacetamide

Product 1

HCID 22272678HCID 22272678, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (2.49 g, 18 mmol) was added to a solution of 2-bromo-N-heptylacetamide (3.30 g, 15 mmol) obtained in Example 16 and 1-(3-hydroxypropyl)piperazine (2.16 g, 15 mmol) in acetonitrile (60 ml) and the mixture was stirred at room temperature for 15 hours. The reaction solution was concentrated and the residue was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution successively and dried over anhydrous sodium carbonate and the residue obtained after 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 4.38 g (yield 97%) of N-heptyl-2-[4-[3-hydroxypropyl]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 and saturated sodium chloride solution successively
  4. dry with materialdried over anhydrous sodium carbonate
  5. customthe residue obtained
  6. customafter evaporation of the solvent
  7. 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-ac9ef636af98456e97893d106cee087e
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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