Water → 6-[4-(2-Phenyl-2-hydroxyethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril monohydrochloride

HRID 477180Notes

Reaction equation

C(C[CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]3)=[O:18])[CH2:13][CH2:12]1)(=O)C1C=CC=CC=1.[ClH:30].NO.[OH2:33]>N1C=CC=CC=1>[ClH:30].[C:19]1([CH:17]([OH:33])[CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]4)=[O:18])[CH2:13][CH2:12]2)[CH:20]=[CH:21][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

20 Grams of 6-[4-(2-benzoylethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril and 5.33 g of hydroxylamine hydrochloride were dispersed in 40 ml of pyridine and the suspension was stirred at 100° C. for 4 hours. After the reaction was completed, the reaction mixture was poured into water and then extracted with chloroform, the extract was dried with anhydrous potassium carbonate, then the solvent was removed by evaporation. The thus obtained residue was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol=50:1), then recrystallized from ethanol to yield 8.79 g of 6-[4-(3-hydroxyimino-3-phenylpropyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril 1/2-hydrate. White powdery substance.

Workup

extractionextracted with chloroform
dry with materialthe extract was dried with anhydrous potassium carbonate
customthe solvent was removed by evaporation
customThe thus obtained residue was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol=50:1)
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-5ccc7394814846f8a920133a453a62f7
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886809

Reaction notes

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