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

HRID 1375941
Notes
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Reaction equation

HRID 1375941 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][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].C[OH:42]>[Pd]>[C:21]([OH:42])(=[O:22])[CH3:23].[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[C:24]([C:29]4[CH:30]=[CH:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=4)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 22499370N-[4-[1-(phenylmethyl)-4-piperidinyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 22499386N-[4-(4-piperidinyl)phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide acetate

Reagents, catalysts & solvents 1

HCID 23938
Palladium
Catalyst

Procedure

A mixture of intermediate (7) (0.025 mole) in methanol (250 ml) was hydrogenated at 50° C. overnight with Pd/C 10% (2 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. A part (0.2 g) of this fraction was purified by high performance liquid chromatography over RP-18 (eluent: (NH4OAc 0.5%/CH3CN 90/10)/CH3OH/CH3CN 75/25/0, 0/50/50, 0/0/100 and 75/25/0; column: Hyperprep RP 100 Å 8 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.119 g of N-[4-(4-piperidinyl)phenyl]-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxamide acetate (1:2) (intermediate 8, melting point 150° C.).

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was triturated in DIPE
  3. filtrationThe precipitate was filtered off
  4. customdried
  5. customA part (0.2 g) of this fraction was purified by high performance liquid chromatography over RP-18 (eluent: (NH4OAc 0.5%/CH3CN 90/10)/CH3OH/CH3CN 75/25/0, 0/50/50, 0/0/100 and 75/25/0; column: Hyperprep RP 100 Å 8 μm)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d26f92438b1647d59e073beec81a0a7c
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07169796B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes