Piperazine → 6-Chloro-1-cyclopropyl-8-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid

HRID 256313Notes

Reaction equation

HRID 256313 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F: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>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[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]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 135791636-Chloro-1-cyclopropyl-7,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 4830976-Chloro-1-cyclopropyl-8-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acidYield 84.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12 g (40 mmoles) of the product from Example A are heated under reflux in 100 ml of pyridine with 17.2 g (0.2 mole) of piperazine for 5 hours. The mixture is concentrated in vacuo, the residue is stirred with 120 ml of water and the mixture is brought to 5 with 2N hydrochloric acid. The precipitate is filtered off with suction, washed with methanol and water, boiled up in 80 ml of methanol and dried. 12.3 g (84% of theory) of 6-chloro-1-cyclopropyl-8-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid of melting point 295°-298° C. (with decomposition) are obtained.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed with methanol and water
  4. customdried

Sources & evidence

ORD record
ord-05d334f84e644ad193b87bf8723852bb
Source dataset
uspto-grants-1987_10
Patent number
US04703047

Reaction notes

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