1-(3-(Trifluoromethyl)phenyl)piperazine → 1-(p-Tolylsulphonyl)-4-(3-(trifluoromethyl)phenyl)piperazine

HRID 1868002Notes

Reaction equation

HRID 1868002 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:12]2[CH2:13][CH2:14][N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=3)[CH2:10][CH2:11]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 73974-Toluenesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 30194181-(p-Tolylsulphonyl)-4-(3-(trifluoromethyl)phenyl)piperazineYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Representative sulfonation (Step 1A): To a stirred solution of 1-(3-(trifluoromethyl)phenyl)piperazine (300 mg, 1.3 mmol) and 4-methylbenzene-1-sulfonyl chloride (248 mg, 1.3 mmol) in anhydrous dichloromethane (3 mL) was added diisopropylethylamine (0.27 mL, 1.6 mmol). The mixture was stirred overnight. Reaction was complete as determined by TLC. The reaction mixture was purified with flash column chromatography to yield 1-(4-methylphenylsulfonyl)-4-[3-(trifluoromethyl)phenyl]piperazine in 81% yield (405 mg) as white solid.

Workup

  1. customReaction
  2. customThe reaction mixture was purified with flash column chromatography

Sources & evidence

ORD record
ord-8f7ee4b39b0e47789e4a22d4e71a4366
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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