1-(2-Methoxyphenyl)piperazine → HCID 21473365, compound

HRID 2293971Notes

Reaction equation

HRID 2293971 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Cl[C:16]1[N:25]=[C:24]2[C:19]([C:20](=[O:38])[C:21]([C:33]([O:35]CC)=[O:34])=[CH:22][N:23]2[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:18][C:17]=1[F:39]>C(O)C>[F:39][C:17]1[CH:18]=[C:19]2[C:24](=[N:25][C:16]=1[N:12]1[CH2:13][CH2:14][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:10][CH2:11]1)[N:23]([C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)[CH:22]=[C:21]([C:33]([OH:35])=[O:34])[C:20]2=[O:38]

Participants

4

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 10926601ethyl 7-chloro-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 21473365HCID 21473365, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 40 ml of ethanol was dissolved 0.81 g (0.0042 mole) of 1-(2-methoxyphenyl)piperazine, and to the solution was added gradually 1.02 g (0.0028 mole) of ethyl 7-chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3carboxylate at 30° C. while stirring. After completion of the addition, the mixture was reacted at the same temperature for 4 hours. After the reaction mixture was cooled, crystals precipitated were collected by filtration and washed with ethanol. To the crystals were added 12 ml of a 6N hydrochloric acid aqueous solution, and the mixture was refluxed by heating for 6 hours. After cooling, the reaction mixture was adjusted to pH 8.5 with a 1N sodium hydroxide aqueous solution, and crystals precipitated were collected by filtration and applied to silica gel column chromatography (the eluent used was a mixture of chloroform:methanol=9.5:0.5) to obtain 0.87 g of the title compound as slightly yellow powder.

Workup

  1. additionAfter completion of the addition
  2. customthe mixture was reacted at the same temperature for 4 hours
  3. temperatureAfter the reaction mixture was cooled
  4. customcrystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed with ethanol
  7. additionTo the crystals were added 12 ml of a 6N hydrochloric acid aqueous solution
  8. temperaturethe mixture was refluxed
  9. temperatureby heating for 6 hours
  10. temperatureAfter cooling
  11. customprecipitated
  12. filtrationwere collected by filtration
  13. additiona mixture of chloroform

Sources & evidence

ORD record
ord-1b60177239d5428cbd2485a025dff4c2
Source dataset
uspto-grants-1997_11
Patent number
US05688791

Reaction notes

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