1-(4-Pyridyl)piperazine → 1-Ethyl-6-fluoro-7-[4-(4-pyridyl)piperazin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1419766Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:28]3[CH2:29][CH2:30][N:25]([C:22]4[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=4)[CH2:26][CH2:27]3)[CH:11]=2)[C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]1)[CH3:13]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 0.31 g of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.33 g of (4-pyridyl)piperazine and 2 ml of pyridine was stirred at 125° C. for 1 hour. After cooling, the reaction mixture was added to ice water to cause crystallization. The resulting crystal was collected by filtration, washed with ethyl ether and then recrystallized from ethanol to yield 0.1 g of the title compound.

Workup

temperatureAfter cooling
customcrystallization
filtrationThe resulting crystal was collected by filtration
washwashed with ethyl ether
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-9573628676ff4a1f9cf6e7c235ed3c36
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05889009

Reaction notes

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