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

HRID 1989853Notes

Reaction equation

HRID 1989853 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:28][C:29]([F:46])([F:45])[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[C:37]([C:42](Cl)=[O:43])=[CH:38][CH:39]=[CH:40][CH:41]=2)=[CH:32][CH:31]=1>C(Cl)Cl>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:42]([C:37]4[C:36]([C:33]5[CH:34]=[CH:35][C:30]([C:29]([F:28])([F:45])[F:46])=[CH:31][CH:32]=5)=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:43])=[CH:18][CH:19]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 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 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[4-(phenylmethyl)-1-piperazinyl]-benzenamine (0.3 mol) and triethylamine (0.36 mol) in DCM (1500 ml) was stirred at room temperature for 15 minutes. 4′-(Trifluoromethyl)-[1,1′-biphenyl]-2-carbonyl chloride (0.36 mol) was added dropwise over 30 minutes. The mixture was stirred at room temperature for 3 hours and then washed twice with water, then washed with a saturated NaCl solution. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was stirred in DIPE (800 ml). The precipitate was filtered off, washed twice with DIPE and dried in vacuo at 50° C., yielding 140.2 g of N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxamide (intermediate 1, mp. 180° C.).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. washwashed twice with water
  3. washwashed with a saturated NaCl solution
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. stirringThe residue was stirred in DIPE (800 ml)
  9. filtrationThe precipitate was filtered off
  10. washwashed twice with DIPE
  11. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-83b8f7893b7c47aeb7d2924ceb12d5cb
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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