Hydrochloric Acid → HCID 69161211, compound

HRID 459858Notes

Reaction equation

HRID 459858 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([C:22]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38]([O:40]CC)=[O:39])=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)=[O:23])[CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[OH-].[Na+].Cl>CO>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([C:22]([N:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:31]=[CH:32][C:33]([CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[CH:34][CH:35]=4)[CH2:28][CH2:29]3)=[O:23])[CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22930993HCID 22930993, compound

Product 1

HCID 69161211HCID 69161211, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a THF (5 ml) and methanol (5 ml) mixed solution of 1.01 g of ethyl 3-(4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl }phenyl)propanoate was added 5 ml of a 1M aqueous sodium hydroxide solution, followed by 1 hour of stirring at room temperature. To the reaction solution was added 5 ml of a 1M aqueous hydrochloric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was evaporated, thus obtained crude crystals were recrystallized from ethanol to obtain 673 mg of 3-(4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}phenyl) propanoic acid as colorless crystals.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter the solvent was evaporated
  5. customthus obtained crude crystals
  6. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-11a9e61034ef4d6bbecf2ea5913e7036
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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