N-3-(4-pentylphenyl)propylphthalimide → 3-(4-Pentylphenyl)propylamine

HRID 1072716Notes

Reaction equation

HRID 1072716 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][N:15]2C(=O)C3=CC=CC=C3C2=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]>C(O)C.[OH-].[Na+]>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][NH2:15])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 22387439N-3-(4-pentylphenyl)propylphthalimide

Product 1

HCID 223875943-(4-Pentylphenyl)propylamineYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-3-(4-pentylphenyl)propylphthalimide (41.1 g, 123 mmol) and hydrazinemonohydrate (9.0 ml, 185 mmol) in ethanol (300 ml) was refluxed for 3 hours. The reaction mixture was dissolved in 5N aqueous sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate anhydride, and the organic layer was concentrated to give the object compound as an oily substance. 13.5 g, (yield 53%)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydride
  4. concentrationthe organic layer was concentrated
  5. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-9d5c4dc7bc1a49ae88ad3e74dd16d6ff
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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