Lithium Hydroxide → HCID 22685869, compound

HRID 404646Notes

Reaction equation

HRID 404646 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([O:13]CC)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Li+].[OH-]>CCO.O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([OH:13])=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 53530378HCID 53530378, compound

Product 1

HCID 22685869HCID 22685869, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-(4-acetylpiperazin-1-yl)-2-phenylacetate (285 mg, 0.98 mmol) was dissolved in a mixture EtOH (6.5 ml) and water (3.3 ml). LiOH (23.5 mg, 0.98 mmol) was added and the reaction was stirred at room temperature overnight. LiOH (23.5 mg, 0.982 mmol) was added again and the mixture was stirred for additional 24 hours. EtOH was evaporated and 1N HCl was added dropwise to the aqueous solution till pH 6-7 before evaporating to dryness. The crude was purified by flash chromatography (DCM/MeOH=75/25) to obtain 2-(4-acetylpiperazin-1-yl)-2-phenylacetic acid (246 mg, 96% yield) as a white solid.

Workup

  1. stirringthe mixture was stirred for additional 24 hours
  2. customEtOH was evaporated
  3. addition1N HCl was added dropwise to the aqueous solution till pH 6-7
  4. custombefore evaporating to dryness
  5. customThe crude was purified by flash chromatography (DCM/MeOH=75/25)

Sources & evidence

ORD record
ord-e68777194c7444878641c5bc29381542
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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