Piperazine → HCID 13960202, compound

HRID 2413959Notes

Reaction equation

HRID 2413959 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([F:21])=[C:19](Cl)[C:12]3=[C:13]2[N:8]([CH:9]([CH3:23])[CH2:10][C:11]3=[O:22])[CH:7]=1)=[O:5])[CH3:2].[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([F:21])=[C:19]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[C:12]3=[C:13]2[N:8]([CH:9]([CH3:23])[CH2:10][C:11]3=[O:22])[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 13960199HCID 13960199, compound

Product 1

HCID 13960202HCID 13960202, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.75 g (0.02 mole) of 8-chloro-9-fluoro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester was suspended in 120 ml of chloroform, 6.89 g (0.08 mole) of piperazine was added thereto, and this mixture was stirred at 20°-25° C. for 6 hours. The resulting reaction solution was concentrated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography [using a chloroform-methanol mixture (with a volume ratio of 10.1) as the developing solvent]. The fraction containing the desired product was evaporated to dryness under reduced pressure and the resulting residue was recrystallized from benzene to obtain 4.79 g (61.8% yield) of 9-fluoro-5-methyl-8-(1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester in the form of yellow crystals.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue thus obtained
  4. customwas purified by silica gel column chromatography [
  5. additionThe fraction containing the desired product
  6. customwas evaporated to dryness under reduced pressure
  7. customthe resulting residue was recrystallized from benzene

Sources & evidence

ORD record
ord-2528333f4d424b8892ed666e4001c97d
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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