Hydrochloric Acid → HCID 66792690, compound

HRID 534928Notes

Reaction equation

HRID 534928 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:20])[C:15]([O:17]CC)=[O:16])[CH2:10][CH2:9]2)=[C:4]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]=1.[OH-].[Li+].Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:20])[C:15]([OH:17])=[O:16])[CH2:10][CH2:9]2)=[C:4]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66792768HCID 66792768, compound

Product 1

HCID 66792690HCID 66792690, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl [4-(4-bromo-2-tert-butylphenyl)piperazin-1-yl](oxo)acetate (Example 66, 0.280 g, 0.705 mmol) in THF (5 mL) stirring at 0° C. was added 1 M lithium hydroxide solution (5 mL, 5 mmol). After 2 h the reaction mixture was acidified with 1 M hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to provide [4-(4-bromo-2-tert-butylphenyl)piperazin-1-yl](oxo)acetic acid (0.241 g, 92%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-40df6698568a4e3e9dab60cc6dd5aa08
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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