Piperazine, hexahydrate → 1-Ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxoquinoline-3-carboxylic acid pentahydrate

HRID 614906

Reaktionsgleichung

[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](Cl)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[OH2:19].O.O.O.O.O.[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>O>[OH2:15].[OH2:19].[OH2:15].[OH2:15].[OH2:15].[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 170 °C

Versuchsvorschrift

A mixture of 1-ethyl-6-fluoro-7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.9g), piperazine hexahydrate (15g) and water (15 ml) was heated at 170° C. in a sealed tube for 16 hr. After evaporation of the solvent, the residue was acidified with diluted hydrochloric acid, heated at 100° C., and the hot solution was filtered. The filtrate was evaporated to dryness. The residue was dissolved in 10% sodium hydroxide and neutralized with acetic acid. The precipitate was collected, washed with water, dried, and recrystallized from ethanol to give 1-ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxoquinoline-3-carboxylic acid pentahydrate (I) as colorless powder, m.p.: 226°-227° C. Mass spectrum m/e: 319 (M+).

Aufarbeitung

customAfter evaporation of the solvent
temperatureheated at 100° C.
filtrationthe hot solution was filtered
customThe filtrate was evaporated to dryness
dissolutionThe residue was dissolved in 10% sodium hydroxide and neutralized with acetic acid
customThe precipitate was collected
washwashed with water
customdried
customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag: ord-3f951248f3f94041966d29418c103210
Quelldatensatz: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04146719

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