4-Aminophenol → 4-(cyclopentyloxy)aniline

HRID 723345Notes

Reaction equation

HRID 723345 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:11]1(Br)[CH2:15][CH2:14][CH2:13][CH2:12]1>CN(C)C=O.O>[CH:11]1([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 4034-AminophenolHCID 8728BromocyclopentaneHCID 24758Sodium hydride

Product 1

HCID 64844484-(cyclopentyloxy)aniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (50% in oil; 4.8 g) was added in portions to a solution of 4-aminophenol (10.9 g) in dimethylformamide (150 ml). After 20 minutes, cyclopentyl bromide (14.9 g) was added dropwise. After 2 hours at room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried and concentrated. The residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 3:1). The product with the molecular weight of 177.25 (C11H15NO); MS (ESI): 178 ([M+H]+), was obtained in this way.

Workup

  1. waitAfter 2 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 3:1)
  7. customMS (ESI): 178 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-907303e753af49d598152bfb20305c3c
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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