N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-4'-(trifluoro-methyl)-[1,1'-biphenyl]-2-carboxamide → 4'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(piperazinyl)-phenyl]-amide

HRID 1989854Notes

Reaction equation

HRID 1989854 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]4[C:24]([C:29]5[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=5)=[CH:25][CH:26]=[CH:27][CH:28]=4)=[O:22])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)C=CC=CC=1.[H][H]>CO.C1COCC1.[Pd]>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]3[C:24]([C:29]4[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:36])[F:38])=[CH:31][CH:30]=4)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:18][CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 2

HCID 22499401N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-4'-(trifluoro-methyl)-[1,1'-biphenyl]-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 112010994'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(piperazinyl)-phenyl]-amide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (1) (0.19 mol) in methanol (600 ml) and THF (600 ml) was hydrogenated overnight with palladium on carbon (10%; 3 g) as a catalyst. After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was triturated in DIPE. The precipitate was filtered off and dissolved in water. The mixture was alkalized with Na2CO3 and then extracted with DCM. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was triturated in DIPE. The precipitate was filtered off and dried, yielding N-[4-(1-piperazinyl)phenyl]-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxamide (intermediate 2).

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was triturated in DIPE
  3. filtrationThe precipitate was filtered off
  4. dissolutiondissolved in water
  5. extractionextracted with DCM
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was triturated in DIPE
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-924f4b2c07ec456294b2e784cf8caad6
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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