N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-[1,1'-biphenyl]-2-carboxamide → N-[4-(1-piperazinyl)phenyl]-[1,1'-biphenyl]-2-carboxamide

HRID 1804429Notes

Reaction equation

HRID 1804429 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][CH:32]=[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.[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:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:18][CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 22499373N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-[1,1'-biphenyl]-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 22499369N-[4-(1-piperazinyl)phenyl]-[1,1'-biphenyl]-2-carboxamideYield 81.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (9) (0.1 mole) in methanol (500 ml) was hydrogenated for two hours with palladium-on-carbon (10%) (10 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 2-propanol. The precipitate was filtered off and dried, yielding 29 g of N-[4-(1-piperazinyl)phenyl]-[1,1′-biphenyl]-2-carboxamide (intermediate 10, melting point 176° C.).

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was triturated in 2-propanol
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-199a44b75cd042d397704bed6b3d428f
Source dataset
uspto-grants-2013_01
Patent number
US08354402B2

Reaction notes

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