N-Hydroxyphthalimide → HCID 14880862, compound

HRID 1710168Notes

Reaction equation

HRID 1710168 reaction equation
[H-].[Na+].[OH:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].Cl[CH2:16][CH2:17][CH2:18][N:19]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23]>CN(C)C=O>[CH2:24]([N:19]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][CH2:17][CH2:16][O:3][N:4]1[C:5](=[O:14])[C:6]2=[CH:13][CH:12]=[CH:11][CH:10]=[C:7]2[C:8]1=[O:9])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 24758Sodium hydrideHCID 96084N-(3-Chloropropyl)dibutylamine

Product 1

HCID 14880862HCID 14880862, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 1.75 g of sodium hydride in ml of N,N-dimethylformamide was added a mixture of 11.9 g of N-hydroxyphthalimide and 60 ml of N,N-dimethylformamide, and then the mixture was stirred for minutes. To the reaction solution was added a mixture of 15 g of 3-chloropropyldibutylamine and 10 ml of N,N-dimethylformamide, and then the mixture was heated at reflux for 5 hours. After evaporation of the solvent, ethyl acetate was added to the residue, and the mixture was washed with water. Evaporation of the solvent gave 23.4 g of N-(3-dibutylaminopropoxy)-phthalimide, which was then dissolved in 200 ml of methylene chloride. To the solution was added 20 ml of hydrazine monohydrate, and the mixture was stirred at room temperature for 3 hours. After removal of the insolubles by filtration, the filtrate was concentrated under reduced pressure and distilled under reduced pressure to give 10.3 g of O-(3-dibutylaminopropyl)hydroxylamine.

Workup

  1. additionwas added
  2. additionTo the reaction solution was added
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 5 hours
  5. customAfter evaporation of the solvent, ethyl acetate
  6. additionwas added to the residue
  7. washthe mixture was washed with water
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-bc6d9cd67fb04e099398d912d6e3640c
Source dataset
uspto-grants-1990_08
Patent number
US04952689

Reaction notes

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