Hydrochloric Acid → HCID 66792774, compound

HRID 534960Notes

Reaction equation

HRID 534960 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:13])=[CH2:12])[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]([C:11]([CH3:13])=[CH2:12])[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)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66751160HCID 66751160, compound

Product 1

HCID 66792774HCID 66792774, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl {4-[2-tert-butyl-4-(1-methylethenyl)phenyl]piperazin-1-yl}(oxo)acetate (Example 166, 0.057 g, 0.158 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 HCl 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-methylethenyl)phenyl]piperazin-1-yl}(oxo)acetic acid (0.057 g, quant.) 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-7dcd7b2aa801485eaf5ae4026c45a540
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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