2-Bromoethyl ethyl ether → HCID 22272760, compound

HRID 1064813Notes

Reaction equation

HRID 1064813 reaction equation
[CH:1]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH:14][C:15](=[O:27])[CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]1)([CH3:3])[CH3:2].[CH2:28]([O:30][CH2:31][CH2:32]Br)[CH3:29]>CN(C=O)C.[F-].[K+]>[CH:1]([C:4]1[C:9]([O:10][CH2:29][CH2:28][O:30][CH2:31][CH3:32])=[CH:8][CH:7]=[C:6]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH:14][C:15](=[O:27])[CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]1)([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 611412-Bromoethyl ethyl etherHCID 69731075HCID 69731075, compound

Product 1

HCID 22272760HCID 22272760, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 522689Potassium FluorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(2,6-diisopropyl-3hydroxyphenyl)-2-[4-(3-hydroxypropyl) piperazin-1-yl]acetamide (180 mg, 0.61 mmol) in DMF (3 ml) were added 2-bromoethyl ethyl ether (2 ml) and potassium fluoride catalyst carried on alumina (40 wt %, 355 mg, 2.39 mmol) followed by stirring at 50° C. for 3 hours. After the catalyst was filtered off, the filtrate was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=20:1) to provide 90 mg (yield 42%) of N-(2,6-diisopropyl-3-(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 ethyl acetate
  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 residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-5f7d4efdc86d4668bf71cd3d9e590a1f
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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