1,5-Dibromopentane → N-(5-Bromopentyl)phthalimide

HRID 1919549Notes

Reaction equation

HRID 1919549 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[K]>CN(C=O)C>[Br:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:12]1[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]2[C:8]1=[O:18]

Participants

4

Reactant 2

HCID 81001,5-DibromopentaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 136770N-(5-Bromopentyl)phthalimideYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,5-dibromopentane (9.00 ml, 65.22 mmol) dissolved in DMF (100 ml) was added potassium phthalimide (12.08 g, 65.22 mmol) at room temperature, and the reaction mixture was stirred for 24 hours. After the reaction was completed, distilled water was added, and the resulting reaction mixture was stirred for 10 minutes and extracted with ethyl acetate three times. Then, the organic phase was washed with a saline solution, dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate:hexane=1:3) to give the target compound (10.6 g, 55%).

Workup

  1. distillationdistilled water
  2. additionwas added
  3. customthe resulting reaction mixture
  4. stirringwas stirred for 10 minutes
  5. extractionextracted with ethyl acetate three times
  6. washThen, the organic phase was washed with a saline solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-13c8eed5f9d14c15ade1be05c86fecbf
Source dataset
uspto-grants-2012_05
Patent number
US08168646B2

Reaction notes

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