Methyl Anthranilate → 1-[N-(2-methoxycarbonylphenyl)-2-aminoethyl]-4-(2-methoxyphenyl)piperazine

HRID 2184834Notes

Reaction equation

HRID 2184834 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].Cl[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])[CH2:17][CH2:16]1.C([O-])(=O)C.[Na+]>O>[CH3:11][O:10][C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])[CH2:19][CH2:20]1)=[O:9]

Participants

5

Reactant 3

HCID 8635Methyl AnthranilateHCID 517045Sodium AcetateHCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 224581781-[N-(2-methoxycarbonylphenyl)-2-aminoethyl]-4-(2-methoxyphenyl)piperazineYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.93 g of methyl anthranilate, 2 g of 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine, 0.88 g of sodium acetate and 5 mL of H2O was stirred for 24 h at reflux. After cooling at room temperature, the mixture was extracted with EtOAc, the organic phase dried on Na2SO4, evaporated to dryness and the residue purified via flash chromatography (CH2Cl2-MeOH 98:2) giving 0.41 g (18%) of the title compound.

Workup

  1. temperatureat reflux
  2. extractionthe mixture was extracted with EtOAc
  3. customthe organic phase dried on Na2SO4
  4. customevaporated to dryness
  5. customthe residue purified via flash chromatography (CH2Cl2-MeOH 98:2)

Sources & evidence

ORD record
ord-f39a6cc6dc724ba99e7da9641b5d7c02
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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