N-3-Bromopropylphthalimide → HCID 68840039, compound

HRID 1725346Notes

Reaction equation

HRID 1725346 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:13])[CH:12]=1)[O:5][CH2:6][CH2:7][NH:8][CH3:9].Br[CH2:15][CH2:16][CH2:17][N:18]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:28].[F-].[K+]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:13])[CH:12]=1)[O:5][CH2:6][CH2:7][N:8]([CH3:9])[CH2:15][CH2:16][CH2:17][N:18]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:28]

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 522689Potassium FluorideHCID 45091395HCID 45091395, compound

Product 1

HCID 68840039HCID 68840039, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of [2-(3,5-difluoro-phenoxy)-ethyl]-methyl-amine (0.63 g, 3.4 mmol), 2-(3-bromo-propyl)-isoindole-1,3-dione (1.03 g, 3.8 mmol), 30% potassium fluoride on Celite® (1.35 g, 7 mmol) and acetonitrile (30 ml) was stirred for 20 hours at 50° C. The solvent was concentrated and the residue was dissolved in ethyl acetate. The Celite was filtered off, the solution was washed with water, then the organic phase was dried over magnesium sulfate and concentrated. The residue was chromatographed on silicagel eluting with methylene chloride-methanol (97-3) to give 2-(3-{[2-(3,5-difluoro-phenoxy)-ethyl]-methyl-amino}-propyl)-isoindole-1,3-dione (1 g, 78.6%).

Workup

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. filtrationThe Celite was filtered off
  4. washthe solution was washed with water
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silicagel
  8. washeluting with methylene chloride-methanol (97-3)

Sources & evidence

ORD record
ord-3ba6d79fb37049ec9a3ebb7a7095b46a
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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