Hydrochloric Acid → HCID 18545465, compound

HRID 1267132Notes

Reaction equation

HRID 1267132 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[C:23]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=4)=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:5])C.[OH-].[Na+].Cl>CCO>[F:37][C:34]([F:35])([F:36])[C:31]1[CH:30]=[CH:29][C:28]([C:23]2[C:22]([C:20]([NH:19][C:16]3[CH:17]=[CH:18][C:13]([N:10]4[CH2:9][CH2:8][N:7]([CH2:6][C:4]([OH:5])=[O:3])[CH2:12][CH2:11]4)=[CH:14][CH:15]=3)=[O:21])=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53913773HCID 53913773, compound

Product 1

HCID 18545465HCID 18545465, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4′-trifluoromethyl-biphenyl-2-carboxylic acid [4-(4-ethoxycarbonylmethyl-piperazin-1-yl)-phenyl]-amide (4.6 g) in EtOH (80 mL) was added 1N sodium hydroxide and the mixture was stirred under reflux for 2 hours. The solution was cooled at room temperature, acidified with concentrated HCl and evaporated to dryness. The solid residue was purified by flash chromatography eluting with CH2Cl2/MeOH/Et3N (70/30/0.2) and the solid was recrystallized from EtOH to give the title compound (4.2 g) as white crystals.

Workup

  1. temperatureunder reflux for 2 hours
  2. customevaporated to dryness
  3. customThe solid residue was purified by flash chromatography
  4. washeluting with CH2Cl2/MeOH/Et3N (70/30/0.2)
  5. customthe solid was recrystallized from EtOH

Sources & evidence

ORD record
ord-0ddb948a053a4f708ba4ba3a03259e14
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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