HCID 13377054, compound → HCID 13377055, compound

HRID 745660Notes

Reaction equation

HRID 745660 reaction equation
[N+:1]([C:4]1[CH:35]=[CH:34][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:26]4=[C:27]5[N:22]([CH:23]([CH3:28])[CH2:24][CH2:25]4)[CH:21]=[C:20]([C:29]([OH:31])=[O:30])[C:19](=[O:32])[C:18]5=[CH:17][C:16]=3[F:33])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)(=O)C>[NH2:1][C:4]1[CH:35]=[CH:34][C:7]([CH2:8][N:9]2[CH2:10][CH2:11][N:12]([C:15]3[C:26]4=[C:27]5[N:22]([CH:23]([CH3:28])[CH2:24][CH2:25]4)[CH:21]=[C:20]([C:29]([OH:31])=[O:30])[C:19](=[O:32])[C:18]5=[CH:17][C:16]=3[F:33])[CH2:13][CH2:14]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 13377054HCID 13377054, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13377055HCID 13377055, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The Compound [II] (0.71 g), mixed with 10% palladium on charcoal (0.2 g) and acetic acid (25 ml), was hydrogenated with the calculated volume of hydrogen under normal pressure at room temperature. After the calculated volume of hydrogen was taken up, palladium on charcoal was filtered, and the filtrate was concentrated to dryness. The residue was dissolved in a small amount of water, and neutralized with 10% sodium hydroxide solution. The resulting precipitate was collected, dried, and purified by column chromatography on silicagel using a mixture of chloroform and ethanol (10:1) as the developing solvent. The purified product was recrystallized from ethanol to give 0.25 g (yield: 37.1%) of 8-[4-(4-aminobenzyl)-1-piperazinyl]-9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid (Compound [I]) as pale yellow needles, m.p. 215.5°-217.5° C. (decompd.).

Workup

  1. filtrationpalladium on charcoal was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe residue was dissolved in a small amount of water
  4. customThe resulting precipitate was collected
  5. customdried
  6. custompurified by column chromatography on silicagel
  7. additiona mixture of chloroform and ethanol (10:1) as the developing solvent
  8. customThe purified product was recrystallized from ethanol

Sources & evidence

ORD record
ord-14c9097ef855485c9f119b87b0d54aab
Source dataset
uspto-grants-1986_07
Patent number
US04599418

Reaction notes

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