Water → 4-(1-phenyl-1H-indazol-3-yl)-1-piperazine carboxylic acid ethyl ester

HRID 359006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 359006
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[N:20][NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2F)[CH2:8][CH2:7]1)=[O:5])[CH3:2].CC(C)([O-])C.[K+].O>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 542902884-[(Phenylhydrazono)(2-fluorophenyl)methyl]-1-piperazine carboxylic acid ethyl ester

Produkt 1

HCID 151170734-(1-phenyl-1H-indazol-3-yl)-1-piperazine carboxylic acid ethyl esterAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution, under nitrogen of 16.2 g of 4-[(phenylhydrazono)(2-fluorophenyl)methyl]-1-piperazine carboxylic acid ethyl ester in 150 ml of tetrahydrofuran was added, dropwise, a solution of 6.0 g of potassium t-butoxide in 60 ml of tetrahydrofuran. The reaction mixture was stirred at room temperature for 16 hrs., poured into water, and extracted with dichloromethane. The extract was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated to an oil. The oil was purified on a Water's Model 500 Preparative High Pressure Liquid Chromatograph utilizing two silica gel columns and hexane/ethyl acetate (3:1 by volume) as the eluent. Concentration of the appropriate fractions yielded 5.3 g (51%) of 4-(1-phenyl-1H-indazol-3-yl)-1-piperazine carboxylic acid ethyl ester.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThe oil was purified on a Water'

Quellen und Nachweise

ORD-Eintrag
ord-2e1ceb4d20d9422eb7d9154bef5886cb
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04999356

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