1-Methylpiperazine → 6-Fluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid

HRID 544220Notes

Reaction equation

HRID 544220 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[C:11](Cl)[CH:12]=2)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[F:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:24]3[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]3)[CH:12]=2)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 127338801-(2-Fluoroethyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 4882616-Fluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidYield 57%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-(2-fluoroethyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (0.72 g) (2.5 millimole), N-methylpiperazine (1.25 g) (12.5 millimole) and 2 ml pyridine was heated at 135°-145° C. for 10 hours. After cooling, the mixture was evaporated under vacuum. The residue was acidified with acetic acid. The undissolved matter was filtered off. The filtrate was neutralized with an aqueous solution of caustic soda. The presipitate was filtered, washed and dried and recrystallized from a mixture of DMF and ethanol. 0.50 g (57%) of 1-(2-fluoroethyl)-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was obtained.

Workup

  1. temperaturewas heated at 135°-145° C. for 10 hours
  2. temperatureAfter cooling
  3. customthe mixture was evaporated under vacuum
  4. filtrationThe undissolved matter was filtered off
  5. filtrationThe presipitate was filtered
  6. washwashed
  7. customdried
  8. customrecrystallized from a mixture of DMF and ethanol

Sources & evidence

ORD record
ord-505bec5fe5de409ab32ea63a0f331475
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

Loading…