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

HRID 2291281Notes

Reaction equation

HRID 2291281 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

4

Reactant 2

HCID 660572-MethylpiperazineHCID 138255151-Cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

Product 1

HCID 143003861-Cyclopropyl-5,6,8-trifluoro-7-(3-methyl 1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 70.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 filtered, 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

  1. customAfter evaporating the reaction mixture under reduced pressure
  2. dissolutionthe residue was dissolved in dilute aqueous ammonia
  3. additiontreated with activated carbon
  4. customThe filtrate was evaporated under reduced pressure
  5. filtrationThe resulting crystals were filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-0ecfbdefcc9842c7bad8baecef2b1af3
Source dataset
uspto-grants-1989_01
Patent number
US04795751

Reaction notes

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