2-Bromoethyl ethyl ether → HCID 22272766, compound

HRID 1064850Notes

Reaction equation

HRID 1064850 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]([NH:14][C:15]2[C:20]([CH:21]([CH3:23])[CH3:22])=[CH:19][C:18]([OH:24])=[CH:17][C:16]=2[CH:25]([CH3:27])[CH3:26])=[O:13])[CH2:7][CH2:6]1.[CH2:28]([O:30][CH2:31][CH2:32]Br)[CH3:29].[F-].[K+]>CN(C=O)C>[CH:21]([C:20]1[CH:19]=[C:18]([O:24][CH2:29][CH2:28][O:30][CH2:31][CH3:32])[CH:17]=[C:16]([CH:25]([CH3:27])[CH3:26])[C:15]=1[NH:14][C:12](=[O:13])[CH2:11][N:8]1[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH2:10][CH2:9]1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 611412-Bromoethyl ethyl etherHCID 522689Potassium FluorideHCID 22272818HCID 22272818, compound

Product 1

HCID 22272766HCID 22272766, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of this acetamide (500 mg, 1.32 mmol) solution in DMF (12 ml) were added 2-bromoethyl ethyl ether (7 ml) and potassium fluoride 40 wt. % on alumina (40 wt. %, 1.96 g, 13.2 mmol), and the mixture was stirred at room temperature for 5 days. After the catalyst was filtered off, the filtrate was diluted with water and extracted with ethylacetate. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was evaporated therefrom. The resulting residue was purified by a silica gel column chromatography (developing solvent; chloroform:methanol=30:1) to provide 448 mg (yield 78%) of N-[2,6-diisopropyl-4-(2-ethoxyethyloxy)phenyl]-2-[4-(3-hydroxypropyl)piperazin-1-yl]acetamide as colorless powdery crystals.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. additionthe filtrate was diluted with water
  3. extractionextracted with ethylacetate
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe resulting residue was purified by a silica gel column chromatography (developing solvent; chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-fd7bd103aad048e698887940a7b1fee2
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

Loading…