Piperazine → HCID 14651215, compound

HRID 2073852Notes

Reaction equation

HRID 2073852 reaction equation
C([C:3]1[N:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])[C:5]2[C:10]([C:11](=[O:16])[C:12]=1[C:13]([OH:15])=[O:14])=[C:9]([CH3:17])[C:8]([F:18])=[C:7](F)[C:6]=2[F:20])C.[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C(#N)C>[F:18][C:8]1[C:9]([CH3:17])=[C:10]2[C:5](=[C:6]([F:20])[C:7]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[N:4]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])[CH:3]=[C:12]([C:13]([OH:15])=[O:14])[C:11]2=[O:16]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 23364547HCID 23364547, compound

Product 1

HCID 14651215HCID 14651215, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.43 g (1.08 mmol) of ethyl 6,7,8-trifluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.37 g (4.30 mmol) of anhydrous piperazine, and 20 ml of acetonitrile was refluxed overnight, cooled to room temperature, and concentrated. The residue was taken up in 10 ml of 6N hydrochloric acid and refluxed for two hours. The mixture was cooled and the solids were filtered. The crude product was suspended in water which was made basic (pH 12), filtered through a fiberglass pad, and neutralized (pH 6.5). The solids were filtered and washed with water and ether to give 0.37 g of the title compound, mp 283°-284° C.

Workup

  1. concentrationconcentrated
  2. temperaturerefluxed for two hours
  3. temperatureThe mixture was cooled
  4. filtrationthe solids were filtered
  5. filtrationfiltered through a fiberglass pad, and neutralized (pH 6.5)
  6. filtrationThe solids were filtered
  7. washwashed with water and ether

Sources & evidence

ORD record
ord-137cba8ee6e443b5bec4adb83a63d8d3
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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