1-Chloro-5-phenylpentane → 2-(5-Phenylpentyl)isoindoline-1,3-dione

HRID 346232Notes

Reaction equation

HRID 346232 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K]>CN(C)C=O>[C:7]1([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:17]2[C:13](=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]2=[O:18])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 5191731-Chloro-5-phenylpentaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 6261932-(5-Phenylpentyl)isoindoline-1,3-dioneYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 24.0 g (0.131 mole) of 1-chloro-5-phenylpentane (Columbia Organics, Camden, S.C.) in 150 mL of dimethylformamide was added 24.3 g (0.131 mole) of potassium phthalimide (Aldrich) and the reaction mixture was heated at reflux under a nitrogen atmosphere for 15 hr. The solvent was evaporated under reduced pressure to heave a viscous, oily residue. The residue was triturated with 200 mL of water and then the mixture was extracted with four 200-mL portions of methylene chloride. The combined methylene chloride extracts were washed with two 200 mL portions of 2N sodium hydroxide solution, twice with 200 mL portions of water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 35.0 g (91%) of title compound as a viscous oil. A sample of this viscous oil was further purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A, PrepPak® 500 silica gel; ethyl acetate-hexanes, 1:10). Fractions containing title compound were combined and the solvents were evaporated under reduced pressure to give purified title compound as a colorless, viscous oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere for 15 hr
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was triturated with 200 mL of water
  5. extractionthe mixture was extracted with four 200-mL portions of methylene chloride
  6. washThe combined methylene chloride extracts were washed with two 200 mL portions of 2N sodium hydroxide solution, twice with 200 mL portions of water
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2660c9c661cf4f7bb191b7d0a714a596
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

Loading…