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

HRID 1868002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1868002
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8f7ee4b39b0e47789e4a22d4e71a4366
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632838B2

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