Hydroxyamine hydrochloride → 6-{4-[3-(4-Chlorobenzoyl)-3-hydroxyliminopropyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril

HRID 477181Notes

Reaction equation

HRID 477181 reaction equation
ClC1C=CC(C([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]4)=[O:17])[CH2:12][CH2:11]2)=O)=CC=1.[ClH:31].[NH2:32][OH:33].[C:34]([O-:37])(=O)[CH3:35].[Na+]>C(O)C.O>[Cl:31][C:18]1[CH:19]=[CH:20][C:25]([C:34]([C:35](=[N:32][OH:33])[CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]([C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]4)=[O:17])[CH2:14][CH2:15]2)=[O:37])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 140997836-{4-[2-(4-Chlorobenzoyl)ethyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril

Product 1

HCID 881243866-{4-[3-(4-Chlorobenzoyl)-3-hydroxyliminopropyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.7 Grams of 6-{4-[2-(4-chlorobenzoyl)ethyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril, 0.83 g of hydroxylamine hydrochloride and 2.29 g of sodium acetate were dissolved in 40 ml of ethanol and 20 ml of water, and the solution was stirred overnight at room temperature. Then the reaction mixture was concentrated under reduced pressure, then the residue thus obtained was extracted with chloroform, the extract was dried with anhydrous sodium carbonate, then the solvent was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol =50:1), then recrystallized from ethanol to yield 1.2 g of 6-{4-[3-(4-chlorobenzoyl)-3-hydroxyliminopropyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril.

Workup

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. extractionwas extracted with chloroform
  4. dry with materialthe extract was dried with anhydrous sodium carbonate
  5. customthe solvent was removed by evaporation
  6. customThe residue thus obtained
  7. customwas purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol =50:1)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a509122c72404ccebe48d933b511434f
Source dataset
uspto-grants-1989_12
Patent number
US04886809

Reaction notes

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