N-[(1-benzyl-4-hydroxypiperidin-4-yl)methyl]-3,3-dimethyl-2-oxoindoline-1-carboxamide → HCID 67233261, Verbindung

HRID 733101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733101
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][NH:16][C:17]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH3:29])([CH3:28])[C:20]2=[O:30])=[O:18])([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>Cl.CO.[OH-].[Pd+2].[OH-]>[OH:14][C:11]1([CH2:15][NH:16][C:17]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH3:28])([CH3:29])[C:20]2=[O:30])=[O:18])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Komponenten

5

Edukt 1

HCID 67231880N-[(1-benzyl-4-hydroxypiperidin-4-yl)methyl]-3,3-dimethyl-2-oxoindoline-1-carboxamide

Produkt 1

HCID 67233261HCID 67233261, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of N-[(1-benzyl-4-hydroxypiperidin-4-yl)methyl]-3,3-dimethyl-2-oxoindoline-1-carboxamide (280 mg, 0.68 mmol, step 1 of Example 12) and palladium hydroxide (80 mg, 20 wt. % Pd on carbon,) in 10% HCl in methanol was stirred under H2 atmosphere for 20 h. The mixture was filtered through a pad of Celite, washed with methanol and the filtrate was concentrated to give pale yellow oil. The residue was chromatographed on silica gel column eluting with CH2Cl2/methanol/NH4OH (10:1:0.2) to give 73 mg (34%) of the title compound as clear yellow oil.

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated
  4. customto give pale yellow oil
  5. customThe residue was chromatographed on silica gel column
  6. washeluting with CH2Cl2/methanol/NH4OH (10:1:0.2)

Quellen und Nachweise

ORD-Eintrag
ord-8a4c0d722a1041168908d85711462e5d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589109B2

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