Hydrochloric Acid → N-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}glycine

HRID 534871Notes

Reaction equation

HRID 534871 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]([NH:19][CH2:20][C:21]([O:23]CC)=[O:22])=[O:18])[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]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66751413Ethyl N-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}glycinate

Product 1

HCID 46931248N-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}glycineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl N-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}glycinate obtained in Example 4 (430 mg), lithium hydroxide monohydrate (420 mg), water (50 mL), and tetrahydrofuran (50 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 (350 mg, 89%) 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-d53d82f953a64ab1ac9b44ca0c223943
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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