N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-4'-(trifluoro-methyl)-[1,1'-biphenyl]-2-carboxamide → HCID 11201099, compound

HRID 852445

Reaction equation

HRID 852445 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 11201099HCID 11201099, compoundYield 49.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (5) (0.19 mole) in methanol (600 ml) and THF (600 ml) was hydrogenated overnight with Pd/C 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, dried, and dissolved in water. The mixture was alkalinized 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 40 g of N-[4-(1-piperazinyl)phenyl]-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxamide (intermediate 6).

Workup

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

Sources & evidence

ORD record
ord-4007bb0b67744df3894341ce59f0a6d3
Source dataset
uspto-grants-2007_08
Patent number
US07253157B2

Linked notes

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