Lithium Hydroxide → 2-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid

HRID 534906Notes

Reaction equation

HRID 534906 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:23])[C:18]([O:20]CC)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:23])[C:18]([OH:20])=[O:19])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66751140Ethyl 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoacetate

Product 1

HCID 667508542-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acidYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoacetate (0.067 g, 0.21 mmol) in THF (3.0 mL) was added a solution of lithium hydroxide (0.025 g, 1.04 mmol) in water (2.0 mL) at room temperature. After 1 h the reaction mixture was extracted with ethyl acetate (1×5.0 mL) and the aqueous solution acidified with 1 M hydrochloric acid to pH 6. The aqueous layer was extracted with 3:1 chloroform/2-propanol (2×10.0 mL). The combined organics were dried (Na2SO4), filtered, and concentrated under reduced pressure providing 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid (0.031 g, 51%) as a white solid.

Workup

  1. extractionAfter 1 h the reaction mixture was extracted with ethyl acetate (1×5.0 mL)
  2. extractionThe aqueous layer was extracted with 3:1 chloroform/2-propanol (2×10.0 mL)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fdac3aeab4c54e0ca5a18377abc646b0
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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