Piperazine → HCID 14651215, compound

HRID 1081429Notes

Reaction equation

HRID 1081429 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 in vacuo. The residue was taken up in 10 mL of 6N hydrochloric acid and refluxed for 2 hours. The mixture was cooled and the solids were collected by filtration. The crude product was suspended in water which was made basic (pH 12), and the resulting solution was filtered through a fiberglass pad, and neutralized (pH 6.5). The solids were collected by filtration, washed with water, ether, and dried to give 0.37 g of the title compound, mp 283°-284° C.

Workup

  1. concentrationconcentrated in vacuo
  2. temperaturerefluxed for 2 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe solids were collected by filtration
  5. filtrationthe resulting solution was filtered through a fiberglass pad, and neutralized (pH 6.5)
  6. filtrationThe solids were collected by filtration
  7. washwashed with water, ether
  8. customdried

Sources & evidence

ORD record
ord-e96276520e9b40cc8ff27acb194b4f90
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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