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

HRID 1005964Notes

Reaction equation

HRID 1005964 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7].[K].[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12>CN(C=O)C>[Br:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:13]1[C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]2[C:9]1=[O:19]

Participants

4

Reactant 2

HCID 81001,5-DibromopentaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 136770N-(5-Bromopentyl)phthalimideYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.7 g of 1,5-dibromopentane and 4.8 g of phthalimide potassium were stirred at 150° C. for 3 hours in 15 ml of DMF. After the DMF was evaporated under reduced pressure, the residue was added with water and ethyl acetate and separated. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to obtain 4.5 g of the title compound (yield: 75%).

Workup

  1. customAfter the DMF was evaporated under reduced pressure
  2. additionthe residue was added with water and ethyl acetate
  3. customseparated
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-fe5296276d344929b5edeb287a837c67
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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