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

HRID 852456Notes

Reaction equation

HRID 852456 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][CH: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]>[NH:8]1[CH2:13][CH2:12][CH:11]([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][CH:32]=[CH:31][CH:30]=4)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 22499413N-[4-[1-(phenylmethyl)-4-piperidinyl]phenyl]-[1,1'-biphenyl]-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 22499414N-[4-(4-piperidinyl)phenyl]-[1,1'-biphenyl]-2-carboxamideYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (18) (0.145 mol) in methanol (500 ml) was hydrogenated at 50° C. during 48 hours 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 and dried, yielding 49 g of N-[4-(4-piperidinyl)phenyl]-[1,1′-biphenyl]-2-carboxamide (intermediate 19).

Workup

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

Sources & evidence

ORD record
ord-268be32b14604599ab47bcec496cdc75
Source dataset
uspto-grants-2007_08
Patent number
US07253157B2

Reaction notes

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