Ethyl Acetate → 3-{(4-Methoxyphenyl)-[1-(4-acetoxyphenyl)ethylamino]methyl}phenylamine

HRID 2269412Notes

Reaction equation

HRID 2269412 reaction equation
[Sn](Cl)Cl.[N+:4]([C:7]1[CH:8]=[C:9]([CH:13]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[NH:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=2)[CH3:16])[CH:10]=[CH:11][CH:12]=1)([O-])=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(O)C>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([CH:13]([NH:14][CH:15]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24](=[O:26])[CH3:25])=[CH:21][CH:22]=2)[CH3:16])[C:9]2[CH:8]=[C:7]([NH2:4])[CH:12]=[CH:11][CH:10]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 18347104N-[(3-nitrophenyl)-(4-methoxyphenyl)methyl]-N-[1-(4-acetoxyphenyl)ethyl]amine

Product 1

HCID 183470763-{(4-Methoxyphenyl)-[1-(4-acetoxyphenyl)ethylamino]methyl}phenylamineYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin (II) chloride (451 mg) was added to a solution of N-[(3-nitrophenyl)-(4-methoxyphenyl)methyl]-N-[1-(4-acetoxyphenyl)ethyl]amine (200 mg) [prepared as described in step (a) above] in ethanol (10 ml). The mixture was heated under reflux for 1 hour. At the end of this time, ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate were added to the reaction mixture. The insoluble material was removed by filtration. The filtrate was separated and the aqueous layer was extracted with ethyl acetate. The ethyl acetate layer and extract were combined, washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. It was then concentrated by evaporation under reduced pressure, to afford the title compound (170 mg) as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe insoluble material was removed by filtration
  4. customThe filtrate was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. extractionThe ethyl acetate layer and extract
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationIt was then concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-c82c44c692bc4a03a548b7e3d019805a
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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