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

HRID 534874Notes

Reaction equation

HRID 534874 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:24])[CH2:18][C:19]([O:21]CC)=[O:20])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].O.Cl>O1CCCC1>[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:24])[CH2:18][C:19]([OH:21])=[O:20])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66750910Ethyl 3-[4-(2-tert-butylphenyl)piperazin-1-yl]-3-oxopropanoate

Product 1

HCID 497642393-[4-(2-Tert-butylphenyl)piperazin-1-yl]-3-oxopropanoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[4-(2-tert-butylphenyl)piperazin-1-yl]-3-oxopropanoate obtained in Example 8 (300 mg), lithium hydroxide monohydrate (840 mg), water (10 mL), and tetrahydrofuran (10 mL) was stirred at room temperature for 3 h. 6 M hydrochloric acid solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (199 mg, 73%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4f6d9f0c890b4d7b90d69cb4e551d300
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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