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

HRID 477176Notes

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°-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-9a6a6ea73ee74987b7d27f19eae57234
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886809

Reaction notes

Loading…