HCID 14608784, compound → HCID 14839099, compound

HRID 1650148Notes

Reaction equation

HRID 1650148 reaction equation
[F:1][C:2]1[C:3]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:4][C:5]2[N:14]3[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]3)=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7](=[O:20])[C:6]=2[CH:21]=1.[H][H]>FC(F)(F)C(O)=O.[Pd]>[F:1][C:2]1[C:3]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:4][C:5]2[N:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7](=[O:20])[C:6]=2[CH:21]=1

Participants

5

Reactant 2

HCID 14608784HCID 14608784, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14839099HCID 14839099, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 0.35 g of ethyl 8-fluoro-9-(4-methyl-1-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5-carboxylate and 0.47 g of 10% palladium-on-carbon in 50 ml of trifluoroacetic acid was shaken under 40 lb. of hydrogen in a Parr apparatus for 18 hours. The mixture was filtered and the solvent evaporated. The concentrate was partitioned between aqueous potassium carbonate and dichloromethane. The organic layer was dried and the solvent removed giving 0.32 g of the desired compound, mp 163°-165° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent evaporated
  3. customThe concentrate was partitioned between aqueous potassium carbonate and dichloromethane
  4. customThe organic layer was dried
  5. customthe solvent removed

Sources & evidence

ORD record
ord-43f16a888dcd45d78fd64238e6c107a2
Source dataset
uspto-grants-1990_05
Patent number
US04923868

Reaction notes

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