Benzenesulfonyl chloride, 3,4-dichloro- → 1-[(3,4-Dichlorophenyl)sulfonyl]-4-[4-fluoro-2-(trifluoromethyl)phenyl]piperazine

HRID 1868079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1868079
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[C:4]([C:14]([F:17])([F:16])[F:15])[CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1[Cl:25].C(N(C(C)C)CC)(C)C>ClCCl>[Cl:18][C:19]1[CH:20]=[C:21]([S:26]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[C:14]([F:16])([F:15])[F:17])[CH2:9][CH2:10]2)(=[O:27])=[O:28])[CH:22]=[CH:23][C:24]=1[Cl:25]

Komponenten

5

Edukt 3

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 81531DiisopropylethylamineHCID 579797591-(4-Fluoro-2-(trifluoromethyl)phenyl)piperazine

Produkt 1

HCID 249060601-[(3,4-Dichlorophenyl)sulfonyl]-4-[4-fluoro-2-(trifluoromethyl)phenyl]piperazineAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 1-(4-fluoro-2-(trifluoromethyl)phenyl)piperazine (386 mg, 1.555 mmol) and 3,4-dichlorobenzene-1-sulfonyl chloride (381.8 mg, 1.555 mmol) in anhydrous dichloromethane (3 mL) was added diisopropylethylamine (1.35 mL, 7.775 mmol). The mixture was stirred at room temperature for 30 minutes. Reaction was complete as determined by TLC. The reaction mixture was diluted with dichloromethane, washed with saturated Na2CO3 (aq.), water then brine. Organic layer was dried over MgSO4. The reaction mixture was purified via flash column chromatography to yield 1-[(3,4-dichlorophenyl)sulfonyl]-4-[4-fluoro-2-(trifluoromethyl)phenyl]piperazine in 75.7% yield (538 mg) as white solid.

Aufarbeitung

  1. customReaction
  2. washwashed with saturated Na2CO3 (aq.), water
  3. dry with materialOrganic layer was dried over MgSO4
  4. customThe reaction mixture was purified via flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-092550881de04d87b5794f8e048e9d16
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632838B2

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