Hydrochloric Acid → HCID 66792758, compound

HRID 534963Notes

Reaction equation

HRID 534963 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:26])[C:21]([O:23]CC)=[O:22])[CH2:16][CH2:15]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:26])[C:21]([OH:23])=[O:22])[CH2:16][CH2:15]1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66750925HCID 66750925, compound

Product 1

HCID 66792758HCID 66792758, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl {4-[2-tert-butyl-4-(1-methylethyl)phenyl]piperazin-1-yl}(oxo)acetate (Example 170, 0.113 g, 0.34 mmol) in THF (5 mL) stirring at 0° C. was added 1 M lithium hydroxide solution (5 mL, 5 mmol). After 1 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-[2-tert-butyl-4-(1-methylethyl)phenyl]piperazin-1-yl}(oxo)acetic acid (0.110 g, 97%) 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-e50597f9caf74a8c93d9d1655f9e1955
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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