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

HRID 1460675Notes

Reaction equation

[CH3:1][N:2]([CH3:5])[CH:3]=[O:4].[Cl:6]CC([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[CH2:14][CH2:13]2)=O.Cl[C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=1)[C:25](N1CCNCC1)=[O:26].[CH2:36]([N:38]([CH2:41]C)[CH2:39]C)C>O>[ClH:6].[C:24]1([CH:25]([OH:26])[CH2:36][N:38]2[CH2:41][CH2:5][N:2]([C:3]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[NH:16][C:15](=[O:20])[CH2:14][CH2:13]4)=[O:4])[CH2:1][CH2:39]2)[CH:23]=[CH:22][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To 60 ml of anhydrous dimethylformamide solution containing 6.7 g of 6-(α-chloroacetyl)-3,4-dihydrocarbostyril was added 11.5 g of 4-(3-chlorobenzoyl)piperazine and 5 ml of triethylamine and the whole mixture was stirred at 50 to 60° C. for 1 hour. The reaction mixture was poured into a large amount of water, and the organic layer was extracted with chloroform. The chloroform layer was washed with water, dried, then chloroform was removed by evaporation. The residue thus obtained was recrystallized from methanol-chloroform to yield 5.5 g of 6-[4-(3-chlorobenzoyl)-1-piperazinylacetyl]-3,4-dihydrocarbostyril 1/2-hydrate in the form of colorless powdery substance. Melting point: 231° C.-234° C.

Workup

extractionthe organic layer was extracted with chloroform
washThe chloroform layer was washed with water
customdried
customchloroform was removed by evaporation
customThe residue thus obtained
customwas recrystallized from methanol-chloroform

Sources & evidence

ORD record: ord-c4ac326aebd54108b464e99ad6876787
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05071856

Reaction notes

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