4-Fluoroaniline → trans-4-(4-Cyano-3-trifluoromethylphenyl)-N-(4-fluorophenyl)-2,5-dimethylpiperazine-1-sulfonamide

HRID 1838258Notes

Reaction equation

HRID 1838258 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=1.[S:21]([NH2:25])(N)(=[O:23])=[O:22].[F:26][C:27]1[CH:33]=[CH:32][C:30](N)=[CH:29][CH:28]=1>N1C=CC=CC=1>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([N:3]2[C@H:2]([CH3:1])[CH2:7][N:6]([S:21]([NH:25][C:30]3[CH:32]=[CH:33][C:27]([F:26])=[CH:28][CH:29]=3)(=[O:23])=[O:22])[C@@H:5]([CH3:8])[CH2:4]2)=[CH:10][C:11]=1[C:17]([F:20])([F:19])[F:18])#[N:14]

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 82267SulfamideHCID 11391932trans-4-(2,5-Dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile

Product 1

HCID 69108864trans-4-(4-Cyano-3-trifluoromethylphenyl)-N-(4-fluorophenyl)-2,5-dimethylpiperazine-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 1.21 g portion of trans-4-(2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile synthesized in Reference Example 1-1 and 2.05 g of sulfamide were heated under reflux for 1.5 hours in 15 ml of pyridine. Next, this was mixed with 4.05 ml of 4-fluoroaniline and again heated under reflux for 4 hours. After evaporation of the solvent, the residue was purified by a silica gel column chromatography to obtain 701 mg of the title compound from toluene-ethyl acetate eluate.

Workup

  1. temperaturewere heated
  2. temperatureagain heated
  3. temperatureunder reflux for 4 hours
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-50d8bb59c75a49fe9182e1b8d5d09c23
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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