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

HRID 1420574Notes

Reaction equation

HRID 1420574 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-6161c0cb550a4df496bc4dbabef9eea2
Source dataset
uspto-grants-2000_06
Patent number
US06071920

Reaction notes

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