Lithium Hydroxide → [4-(3,3-diphenyl-propionyl)-piperazin-1-yl]-acetic Acid

HRID 456429Notes

Reaction equation

HRID 456429 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:27])[CH2:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][CH2:7]1)C.[Li+].[OH-]>CO.O>[C:21]1([CH:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:13][C:12]([N:9]2[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:28])=[O:3])[CH2:7][CH2:8]2)=[O:27])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58817810[4-(3,3-diphenyl-propionyl)-piperazin-1-yl]-acetic Acid Ethyl Ester

Product 1

HCID 18437004[4-(3,3-diphenyl-propionyl)-piperazin-1-yl]-acetic AcidYield 78%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of [4-(3,3-diphenyl-propionyl)-piperazin-1-yl]-acetic acid ethyl ester (1.17 g, 3.07 mmol) and LiOH (645 mg, 15.35 mmol) in MeOH: H2O (3:1, 40 ml) stirred at room temperature for 2 days. The solvent was then evaporated and residue dissolved in water. Upon acidified with 2N HCl to pH 3, product precipitated in aq. phase, filtered and washed few times with water and dried to give the desired product in 78% yield.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionresidue dissolved in water
  3. customprecipitated in aq. phase
  4. filtrationfiltered
  5. washwashed few times with water
  6. customdried

Sources & evidence

ORD record
ord-ab4b2667b017452a9e359a6229a1bf05
Source dataset
uspto-grants-2007_03
Patent number
US07186726B2

Reaction notes

Loading…