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

HRID 1464612Notes

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. Melting point: 167°-169° C. (decomp.)

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-b7958d7c79a4402c98007f780a0783c9
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05306719

Reaction notes

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