Sodium Hydroxide → HCID 14969529, compound

HRID 266802Notes

Reaction equation

HRID 266802 reaction equation
C[O:2][C:3]([C:5]1[CH:29]=[CH:28][C:8]([C:9]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][C:18]3=[O:19])[CH2:13][CH2:12]2)=[O:10])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][C:18]3=[O:19])[CH2:15][CH2:16]2)=[O:10])=[CH:28][CH:29]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14969528HCID 14969528, compound

Product 1

HCID 14969529HCID 14969529, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(4-Methoxycarbonylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (6.33 g) and sodium hydroxide (1.94 g) are dissolved in methanol (100 ml) and the mixture is stirred at room temperature overnight. After the solvent is concentrated, water is added to the residue and the mixture is extracted with diethyl ether. The aqueous layer is adjusted to pH 1 by adding conc. hydrochloric acid and extracted with ethyl acetate. The extract is dried with magnesium sulfate, concentrated and recrystallized from n-hexane/ethanol to give 1-[1-(4-carboxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (4.5 g) as white powder, m.p.: 232°-235° C.

Workup

  1. concentrationAfter the solvent is concentrated
  2. additionwater is added to the residue
  3. extractionthe mixture is extracted with diethyl ether
  4. additionby adding conc. hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract is dried with magnesium sulfate
  7. concentrationconcentrated
  8. customrecrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-35c9d768e1114d8996dc3b6ef82fc569
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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