Potassium Hydroxide → HCID 22353140, compound

HRID 895351Notes

Reaction equation

HRID 895351 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[NH2:35])[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[CH2:7][CH2:6]1.[OH-].[K+]>CO>[NH2:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH:11]([N:8]1[CH2:7][CH2:6][N:5]([CH2:4][C:3]([OH:36])=[O:2])[CH2:10][CH2:9]1)[CH2:12][O:13][CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:16]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86590289HCID 86590289, compound2×

Product 1

HCID 22353140HCID 22353140, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a round-bottomed flask were introduced {4-[1-(2-Amino-phenyl)-2-(3,5-bis-trifluoromethyl-benzyloxy)-ethyl]-piperazin-1-yl}-acetic acid methyl ester (compound 323; 1.3 g, 2.5 mmoles), KOH (0.35 g, 6.3 mmoles) and MeOH (20 ml). The reaction mixture was stirred at room temperature for 6 hours. MeOH was removed under reduce pressure and the residue was taken up in water. The pH was adjusted to 6 and the solution was extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated. The residue (1.1 g, 88%) was recrystallized from diethylether to give {4-[1-(2-Amino-phenyl)-2-(3,5-bis-trifluoromethyl-benzyloxy)-ethyl]-piperazin-1-yl}-acetic acid (compound 324; 0.75 g, 60%) as white needles.

Workup

  1. customMeOH was removed
  2. extractionthe solution was extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue (1.1 g, 88%) was recrystallized from diethylether

Sources & evidence

ORD record
ord-25ce9cf7a74f42ff90beb36f096e9b89
Source dataset
uspto-grants-2005_07
Patent number
US06916797B2

Reaction notes

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