Sodium Hydroxide → HCID 19031197, compound

HRID 1708286Notes

Reaction equation

HRID 1708286 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28]C(=O)C)[CH:25]=[CH:24][C:4]=1[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([N:13]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][C:14]2=[O:15])[CH2:9][CH2:8]1)=[O:6].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:4]=1[C:5]([N:7]1[CH2:8][CH2:9][CH:10]([N:13]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][C:14]2=[O:15])[CH2:11][CH2:12]1)=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19031080HCID 19031080, compound

Product 1

HCID 19031197HCID 19031197, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(2-Methoxy-4-acetyloxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (0.4 g) and sodium hydroxide (0.5 g) are dissolved in methanol (20 ml) and the mixture is stirred at room temperature for 1 hour. The solvent is concentrated and water is added to the residue, then the mixture is extracted with chloroform, dried with magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) to give 1-[1-(2-methoxy-4-hydroxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (0.3 g).

Workup

  1. concentrationThe solvent is concentrated
  2. additionwater is added to the residue
  3. extractionthe mixture is extracted with chloroform
  4. dry with materialdried with magnesium sulfate
  5. distillationThe solvent is distilled off
  6. customthe resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-6d2e8405c9ad492c865e426244273c3c
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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