Potassium Iodide → 2-{2-[2-(3-Methoxyphenyl)-1-pyrrolidinyl]ethyl}-1H-isoindole-1,3(2H) dione

HRID 1742260Notes

Reaction equation

HRID 1742260 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:7][CH:8]=1.Br[CH2:15][CH2:16][N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH2:15][CH2:16][N:17]2[C:18](=[O:27])[C:19]3[C:20](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:22])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 36138242-(3-Methoxyphenyl)pyrrolidine

Product 1

HCID 152913732-{2-[2-(3-Methoxyphenyl)-1-pyrrolidinyl]ethyl}-1H-isoindole-1,3(2H) dioneYield 55.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)pyrrolidine (1.9 g) in dry acetonitrile (50 ml) was added N-(2-bromoethyl)phthalimide (3.6 g) followed by milled potassium carbonate (3.8 g) and potassium iodide (catalytic amount) at ambient temperature, under nitrogen. The reaction mixture was warmed under reflux for 18.5 hrs, cooled to ambient temperature and filtered through a pad of celite. The filter cake was washed with ethyl acetate, and the combined filtrates were concentrated. The residue was diluted with ether and methanol, the mixture was filtered, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, dichloromethane). The appropriate fractions were collected and concentrated to afford a total 2.1 g (54%) of product. Recrystallization from ether gave the analytical sample, mp 110°-111° C.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureunder reflux for 18.5 hrs
  3. filtrationfiltered through a pad of celite
  4. washThe filter cake was washed with ethyl acetate
  5. concentrationthe combined filtrates were concentrated
  6. additionThe residue was diluted with ether and methanol
  7. filtrationthe mixture was filtered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by flash column chromatography (silica gel, dichloromethane)
  10. customThe appropriate fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-bdd793144fa443789cdca881b0ffc5f3
Source dataset
uspto-grants-1994_08
Patent number
US05338739

Reaction notes

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