Hydrochloric Acid → 3-[4-(2-Tert-butyl-4-methylphenyl)piperazin-1-yl]-3-oxopropanoic acid

HRID 534945Notes

Reaction equation

HRID 534945 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:25])[CH2:19][C:20]([O:22]CC)=[O:21])[CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[N:12]1[CH2:13][CH2:14][N:15]([C:18](=[O:25])[CH2:19][C:20]([OH:22])=[O:21])[CH2:16][CH2:17]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66750839Ethyl 3-[4-(2-tert-butyl-4-methylphenyl)piperazin-1-yl]-3-oxopropanoate

Product 1

HCID 667513293-[4-(2-Tert-butyl-4-methylphenyl)piperazin-1-yl]-3-oxopropanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 3-[4-(2-tert-butyl-4-methylphenyl)piperazin-1-yl]-3-oxopropanoate (Example 83, 0.210 g, 0.61 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 to evaporated under reduced pressure to provide 3-[4-(2-tert-butyl-4-methylphenyl)piperazin-1-yl]-3-oxopropanoic acid (0.186 g, 96%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-46aa5fa2ce6043a08fd820e879a900be
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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