Piperazine → 7-(1-Piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1638689Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1F)[N:8]([CH:14]1[CH2:16][CH2:15]1)[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[C:5]2=[O:20].[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CN1CCCC1=O>[N:21]1([C:11]2[C:10]([CH3:13])=[C:9]3[C:4]([C:5](=[O:20])[C:6]([C:17]([OH:19])=[O:18])=[CH:7][N:8]3[CH:14]3[CH2:16][CH2:15]3)=[CH:3][C:2]=2[F:1])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

Conditions

Temperature: 150 °C

Procedure

6,7-Difluoro-1-cyclopropyl-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.8 g) is suspended in N-methylpyrrolidone (5 ml) and thereto is added piperazine (1.8 g), and the mixture is stirred at 150° C. for 3 hours. After the reaction, the reaction mixture is concentrated, and the resulting residue is purified by silica gel column chromatography (solvent, dichloromethane:methanol=3:1) to give 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.06 g), as white crystals, m.p. 291°-295° C. (decomp.).

Workup

customAfter the reaction
concentrationthe reaction mixture is concentrated
customthe resulting residue is purified by silica gel column chromatography (solvent, dichloromethane:methanol=3:1)

Sources & evidence

ORD record: ord-493ad33047644231b7309f240be2b5f1
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04880806

Reaction notes

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