2-Methylpiperazine → 5-Benzylamino-1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 373526Notes

Reaction equation

HRID 373526 reaction equation
[CH2:1]([NH:8][C:9]1[C:18]([F:19])=[C:17](F)[CH:16]=[C:15]2[C:10]=1[C:11](=[O:27])[C:12]([C:24]([OH:26])=[O:25])=[CH:13][N:14]2[CH:21]1[CH2:23][CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][CH:29]1[CH2:34][NH:33][CH2:32][CH2:31][NH:30]1>N1C=CC=CC=1>[CH2:1]([NH:8][C:9]1[C:18]([F:19])=[C:17]([N:33]2[CH2:32][CH2:31][NH:30][CH:29]([CH3:28])[CH2:34]2)[CH:16]=[C:15]2[C:10]=1[C:11](=[O:27])[C:12]([C:24]([OH:26])=[O:25])=[CH:13][N:14]2[CH:21]1[CH2:23][CH2:22]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 660572-MethylpiperazineHCID 148802085-Benzylamino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 157294115-Benzylamino-1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 79.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3.0 g of 5-benzylamino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 2.5 g of 2-methylpiperazine and 30 ml of pyridine was heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the solution was acidified with acetic acid and treated with activated charcoal. It was then neutralized with aqueous ammonia. The crystals which precipitated were collected by filtration to give 2.9 g of 5-benzylamino-1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. m.p. 129°-130° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. additiontreated with activated charcoal
  6. customThe crystals which precipitated
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-28f97a0a52464ceab8e371799c8ee099
Source dataset
uspto-grants-1992_11
Patent number
US05164392

Reaction notes

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