N-(2-Phenoxyphenyl)-N-{[2-(prop-1-en-1-yl)phenyl]methyl}acetamide → N-acetyl-N-(2-propylbenzyl)-2-phenoxyaniline

HRID 1016584Notes

Reaction equation

HRID 1016584 reaction equation
[C:1]([N:4]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]=[CH:26][CH3:27])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2]>C(O)C.[Pt]=O>[C:1]([N:4]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][CH3:27])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 70134079N-(2-Phenoxyphenyl)-N-{[2-(prop-1-en-1-yl)phenyl]methyl}acetamide

Product 1

HCID 18407203N-acetyl-N-(2-propylbenzyl)-2-phenoxyanilineYield 85%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

In 7 ml of ethanol was dissolved 757 mg of N-acetyl-N-[2-(propen-1-yl)benzyl]-2-phenoxyaniline (a mixture of the geometrical isomers at a ratio of about 3:2), and 15 mg of platinum oxide was added, followed by stirring under a hydrogen atmosphere at room temperature for 3 hours. The catalyst in the reaction solution was removed by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4) to give 647 mg of N-acetyl-N-(2-propylbenzyl)-2-phenoxyaniline as an oil.

Workup

  1. additionwas added
  2. customThe catalyst in the reaction solution was removed by filtration
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4)

Sources & evidence

ORD record
ord-e5dd8c2d15364d54b8fc122af2b79cd4
Source dataset
uspto-grants-2002_11
Patent number
US06476056B2

Reaction notes

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