Sodium Hydroxide → HCID 14969529, compound

HRID 1648565Notes

Reaction equation

HRID 1648565 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-84f79a563e9646e4b27266b98a8bd226
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

Loading…