HCID 67086685, compound → HCID 67286401, compound

HRID 1665195Notes

Reaction equation

HRID 1665195 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[C:6]([Cl:22])[CH:5]=1>[OH-].[Na+].C1COCC1>[Cl:22][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH3:11])[C:7]=1[O:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[C:3]([OH:23])=[O:2]

Participants

4

Reactant 1

HCID 67086685HCID 67086685, compound

Product 1

HCID 67286401HCID 67286401, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-Chloro-5-methoxy-4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-benzoic acid methyl ester (3.7 g, 10.7 mmol) in 2 N NaOH (20 ml) and THF (40 ml) is heated at reflux for 1 hour. The reaction mixture is washed with Et2O. The aqueous phase is concentrated in vacuo, and water (50 ml) is added. The pH is adjusted to 3-4 using 2 N HCl. To this solution is added DOWEX 50WX4 (previously washed with MeOH, 2 N HCl and water), and the resulting mixture is stirred at room temperature for 1 hour. The resin is filtered, washed with water, and the product is released from the resin by washing with MeOH/NH4OH. The solution is concentrated in vacuo, diluted with DCM and MeOH, dried (Na2SO4) and the solvent removed in vacuo to yield the title compound as a light cream solid.

Workup

  1. temperatureat reflux for 1 hour
  2. washThe reaction mixture is washed with Et2O
  3. concentrationThe aqueous phase is concentrated in vacuo, and water (50 ml)
  4. additionis added
  5. additionTo this solution is added DOWEX 50WX4 (
  6. washpreviously washed with MeOH, 2 N HCl and water), and the resulting mixture
  7. filtrationThe resin is filtered
  8. washwashed with water
  9. washby washing with MeOH/NH4OH
  10. concentrationThe solution is concentrated in vacuo
  11. additiondiluted with DCM and MeOH
  12. dry with materialdried (Na2SO4)
  13. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8d8d5a6050104ce9b70bd314205d345c
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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