Dichloromethane → N-[2-(1-piperidinyl)-5-(trifluoromethyl)phenyl]-p-toluenesulfonamide

HRID 2195650Notes

Reaction equation

HRID 2195650 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.ClCCl.[N:22]1([C:28]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:29]=2[NH2:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>O>[N:22]1([C:28]2[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:38])[F:36])=[CH:31][C:29]=2[NH:30][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 6947562-(Piperidin-1-yl)-5-(trifluoromethyl)aniline

Product 1

HCID 23149633N-[2-(1-piperidinyl)-5-(trifluoromethyl)phenyl]-p-toluenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Toluenesulfonyl chloride (233 g, 1.22 mmol, commercially available product) and triethylamine (254 μl, 1.83 mmol) were sequentially added at room temperature to a dichloromethane (5 ml) solution of 2-(1-piperidinyl)-5-(trifluoromethyl)aniline (149 mg, 0.610 mmol), obtained as described in Referential Example 1-2. The resulting mixture was stirred for 60 hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=10/1). Thus, N-[2-(1-piperidinyl)-5-(trifluoromethyl)phenyl]-p-toluenesulfonamide (GIF-0622) (243 mg, quant) was yielded as a colorless solid.

Workup

  1. customobtained
  2. extractionthe resulting mixture was extracted three times with ethyl acetate
  3. washThe obtained organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-0b04a4357ddd430a95342e98de22c331
Source dataset
uspto-grants-2012_12
Patent number
US08338362B2

Reaction notes

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