2-Methylpiperazine → 1-Cyclopropyl-5,6,8-trifluoro-7-(3-methyl 1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 477012Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (910 mg), 2-methylpiperazine (320 mg, and pyridine (10 ml) was stirred at 80° C. for 1 hour. After evaporating the reaction mixture under reduced pressure, the residue was dissolved in dilute aqueous ammonia and treated with activated carbon. The filtrate was evaporated under reduced pressure and adjusted to pH 7-8. The resulting crystals were collected by filtration, washed with water, and dried to give 1-cyclopropyl-5,6,8-trifluoro-7-(3-methyl 1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (810 mg), m.p. 235°-237° C.

Workup

customAfter evaporating the reaction mixture under reduced pressure
dissolutionthe residue was dissolved in dilute aqueous ammonia
additiontreated with activated carbon
customThe filtrate was evaporated under reduced pressure
filtrationThe resulting crystals were collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-a350ed60f7664efa814b4657c4c2efb2
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886810

Reaction notes

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