Water → HCID 88124585, compound

HRID 483519Notes

Reaction equation

HRID 483519 reaction equation
[CH:1]([C:3]1[CH:27]=[CH:26][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][C:16]3=[O:17])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)=O.Cl.[NH2:29][OH:30].C([O-])(=O)C.[Na+].O>C(O)C>[OH:30][N:29]=[CH:1][C:3]1[CH:27]=[CH:26][C:6]([C:7]([N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][C:16]3=[O:17])[CH2:13][CH2:14]2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 190308281-[1-(4-Formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril

Product 1

HCID 88124585HCID 88124585, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[1-(4-Formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (1 g), hydroxylamine hydrochloride (580 mg) and sodium acetate (1.6 g) are dissolved in ethanol (20 ml) and water (10 ml) and the mixture is stirred at room temperature overnight. The solvent is concentrated and water is added to the residue. The mixture is extracted with chloroform, dried with sodium carbonate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:2) and recrystallized from n-hexane/ethanol to give 1-[1-(4-hydroxyiminomethylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (1 g) as white powder, m.p.: 222°-224° C.

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 sodium carbonate
  5. distillationThe solvent is distilled off
  6. customthe resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:2)
  7. customrecrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-ec6a52e81fe74aaba22fdc5358b96166
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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