3-(Difluoromethoxy)benzenesulfonyl chloride → 4-[5-(3-Difluoromethoxy-benzenesulfonylamino)-2-methoxy-phenyl]-piperazine-1-carboxylic Acid tert-butyl Ester

HRID 1710598

Reaktionsgleichung

Reaktionsgleichung von HRID 1710598
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:23][CH:24]([F:36])[O:25][C:26]1[CH:27]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([NH:20][S:32]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([O:25][CH:24]([F:23])[F:36])[CH:27]=3)(=[O:34])=[O:33])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 27782263-(Difluoromethoxy)benzenesulfonyl chlorideHCID 10686178Tert-butyl 4-(5-amino-2-methoxyphenyl)piperazine-1-carboxylate

Produkt 1

HCID 576995064-[5-(3-Difluoromethoxy-benzenesulfonylamino)-2-methoxy-phenyl]-piperazine-1-carboxylic Acid tert-butyl EsterAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

0.745 g of 4-(5-Amino-2-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (2.423 mmol) were dissolved in 35 ml of pyridine. 0.588 g of 3-(difluoromethoxy)-benzene-sulfonylchloride were added dropwise and the reaction mixture was stirred for 72 h at room temperature. The solvent was evaporated, the residue was dissolved in 40 ml dichloromethane and the organic phase was washed twice with 30 ml aqueous saturated ammonium chloride. The organic phase was dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified three times via silica gel chromatography using dichloromethane-methanol, and dichloromethane-ethyl acetate as eluent. 0.94 g of the title compound were isolated.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 40 ml dichloromethane
  3. washthe organic phase was washed twice with 30 ml aqueous saturated ammonium chloride
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe crude product was purified three times via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0e696af7ba8c420c99894e94d037ad6f
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790727B2

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