Piperazine, hexahydrate → HCID 10714850, compound

HRID 544231Notes

Reaction equation

[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([F:19])=[C:15](Cl)[CH:16]=2)[C:11](=[O:20])[C:10]([C:21]([OH:23])=[O:22])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.O.O.O.O.[NH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([F:19])=[C:15]([N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[CH:16]=2)[C:11](=[O:20])[C:10]([C:21]([OH:23])=[O:22])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 120181Piperazine, hexahydrate

HCID 12733884HCID 12733884, compound

Product 1

HCID 10714850HCID 10714850, compoundYield 79.1%

Procedure

A mixture of 1-benzyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 1.1 g and piperazine hexahydrate 10 g was heated in a sealed tube at 125°-135° C. (inner temperature) for 22 hours. After cooling, the reaction mixture was evaporated under vacuum. The residue was dissolved in warm acetic acid and the insoluble matters was filtered off. The filtrate was neutralized with an aqueous solution of NaOH, and the precipitated crystals were collected by filtration, washed with water and dried. Recrystallizing the crystals from dimethylformamide, 1.0 g (79%) of 1-benzyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid was obtained. Colorless powders.

Workup

temperaturewas heated in a sealed tube at 125°-135° C. (inner temperature) for 22 hours
temperatureAfter cooling
customthe reaction mixture was evaporated under vacuum
dissolutionThe residue was dissolved in warm acetic acid
filtrationthe insoluble matters was filtered off
filtrationthe precipitated crystals were collected by filtration
washwashed with water
customdried
customRecrystallizing the crystals from dimethylformamide

Sources & evidence

ORD record: ord-7a9948e7ec1c49a6ab0e7c1581d34a88
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04448962

Reaction notes

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