4-(4-Benzylpiperazin-1-yl)aniline → N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-4'-(trifluoro-methyl)-[1,1'-biphenyl]-2-carboxamide

HRID 1804425Notes

Reaction equation

HRID 1804425 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15](Cl)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[C:20]1([CH2:26][N:27]2[CH2:32][CH2:31][N:30]([C:33]3[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=3)[CH2:29][CH2:28]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl.C(N(CC)CC)C>[C:20]1([CH2:26][N:27]2[CH2:28][CH2:29][N:30]([C:33]3[CH:34]=[CH:35][C:36]([NH:39][C:15]([C:10]4[C:9]([C:6]5[CH:7]=[CH:8][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][CH:5]=5)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[O:16])=[CH:37][CH:38]=3)[CH2:31][CH2:32]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 7372594-(4-Benzylpiperazin-1-yl)anilineHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

Product 1

HCID 22499401N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-4'-(trifluoro-methyl)-[1,1'-biphenyl]-2-carboxamideYield 104.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 4′-(trifluoromethyl)[1,1′-biphenyl]-2-carbonyl chloride (0.185 mole) in DCM (1500 ml) and triethylamine (50 ml) was stirred on an ice-bath for 5 minutes. 4-[4-(Phenylmethyl)-1-piperazinyl]-benzenamine (0.37 mole) in DCM (500 ml) was added dropwise. The mixture was stirred for 3 hours. The organic layer was separated, washed with water, dried, filtered and the solvent was evaporated. The residue was triturated in DIPE. The precipitate was filtered off and dried, yielding 99.8 g of N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-4′-(trifluoro-methyl)[1,1′-biphenyl]-2-carboxamide (intermediate 5, melting point 180° C.).

Workup

  1. stirringThe mixture was stirred for 3 hours
  2. customThe organic layer was separated
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was triturated in DIPE
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-7c0d459a60b944c48b084adfe967121a
Source dataset
uspto-grants-2013_01
Patent number
US08354402B2

Reaction notes

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