4-Toluenesulfonyl chloride → 1-[(4-Methylphenyl)sulfonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine

HRID 1863014Notes

Reaction equation

HRID 1863014 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:27]=[CH:26][C:17]([C:18]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[O:19])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>O1CCCC1.C(N(CC)CC)C>[CH3:40][C:30]1[CH:35]=[CH:34][C:33]([S:36]([N:23]2[CH2:24][CH2:25][N:20]([C:18](=[O:19])[C:17]3[CH:26]=[CH:27][C:14]([NH:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([C:2]([F:1])([F:28])[F:29])=[CH:4][CH:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:15][CH:16]=3)[CH2:21][CH2:22]2)(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 30552431-Piperazinyl(4-((7-(trifluoromethyl)-4-quinolinyl)amino)phenyl)methanone

Product 1

HCID 203928971-[(4-Methylphenyl)sulfonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazineYield 90.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a suspension of 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine (2 g, 0.005 mol) in 20 ml of tetrahydrofuran and 0.5 ml of triethylamine is added a solution of p-toluenesulfonyl chloride (0.95 g, 0.005 mol) in 10 ml of tetrahydrofuran dropwise over a 15 minute period, under nitrogen. After complete addition, the resultant solution is stirred at room temperature for 1 hour. This is quenched in cold water and extracted with methylene chloride (2×, 50 ml). The methylene chloride solution is washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to a yellow solid. This, after re-crystallization from methanol, gives 2.5 g (90%) of white crystalline 1-[(4-methylphenyl)sulfonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine with melting point 215°-217° C.

Workup

  1. additionAfter complete addition
  2. customThis is quenched in cold water
  3. extractionextracted with methylene chloride (2×, 50 ml)
  4. washThe methylene chloride solution is washed with water, saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to a yellow solid
  7. customThis, after re-crystallization from methanol

Sources & evidence

ORD record
ord-a67702a46fb147ec83e1a15e1a1a16a6
Source dataset
uspto-grants-1979_09
Patent number
US04167567

Reaction notes

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