Ammonium Chloride → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-acetylindoline

HRID 1790445

Reaktionsgleichung

Reaktionsgleichung von HRID 1790445
C([Li])CCC.[F:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25](Br)[CH:26]=4)[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[CH3:31][C:32](N(C)C)=[O:33].[Cl-].[NH4+]>CCCCCC.O1CCCC1.C(OCC)(=O)C>[F:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:32](=[O:33])[CH3:31])[CH:26]=4)[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 220378891-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-bromoindolineHCID 178418339Butyllithium

Produkt 1

HCID 220381171-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-acetylindolineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 2.5 M solution (1.5 ml) of n-butyllithium in hexane was added dropwise at −78° C. into a solution (30 ml) of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoindoline (1.0 g) in tetrahydrofuran over 5 min. After 10 min, dimethylacetamide (0.34 ml) was added thereto and the resultant mixture was warmed to room temperature. Next, a saturated aqueous solution of ammonium chloride and ethyl acetate were added thereto to and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (250 mg) as a yellow powder (yield: 27%).

Aufarbeitung

  1. customto and the layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-e3eec821340f44e9a277867fc7a6326b
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071201B2

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