2-Chloro-5-[4-(2-dimethylamino-ethyl)-piperazin-1-yl]-benzoic acid ethyl ester → 2-Chloro-5-[4-(2-dimethylaminoethyl)-piperazin-1-yl]-benzoic acid

HRID 2047364Notes

Reaction equation

HRID 2047364 reaction equation
C([O:3][C:4](=[O:23])[C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[Cl:22])C>CCO.[OH-].[Na+]>[Cl:22][C:6]1[CH:7]=[CH:8][C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH2:15][CH2:16]2)=[CH:10][C:5]=1[C:4]([OH:23])=[O:3]

Participants

4

Reactant 1

HCID 686703542-Chloro-5-[4-(2-dimethylamino-ethyl)-piperazin-1-yl]-benzoic acid ethyl ester

Product 1

HCID 686700692-Chloro-5-[4-(2-dimethylaminoethyl)-piperazin-1-yl]-benzoic acidYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-chloro-5-[4-(2-dimethylamino-ethyl)-piperazin-1-yl]-benzoic acid ethyl ester (0.46 g, 1.36 mmol) in EtOH (6 mL) and NaOH 10% (2 mL) was heated at reflux overnight, then the reaction mixture was cooled to room temperature and the organic solvent concentrated by evaporation under reduced pressure. The resulting solution was neutralized by dropwise addition of 1N HCl and the water was then evaporated under reduced pressure. The resulting residue was dissolved in EtOH (10 mL), the insoluble material was filtered off and the filtrate concentrated under reduced pressure at room temperature, to obtain 0.24 g of the title compound (58%) without additional purification.

Workup

  1. temperatureat reflux overnight
  2. concentrationthe organic solvent concentrated by evaporation under reduced pressure
  3. additionThe resulting solution was neutralized by dropwise addition of 1N HCl
  4. customthe water was then evaporated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in EtOH (10 mL)
  6. filtrationthe insoluble material was filtered off
  7. concentrationthe filtrate concentrated under reduced pressure at room temperature

Sources & evidence

ORD record
ord-62e3c404776b437ba0e053aae2eda4b1
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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