Potassium Carbonate → 4-(4-Fluorobenzyl)-1-(2-(2-oxo-1,3-dihydroindol-5-oxy)ethyl)piperidine

HRID 1955257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1955257
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:11][CH2:12][CH2:13]OS(C3C=CC(C)=CC=3)(=O)=O)[CH:8]=2)[NH:3]1.[F:25][C:26]1[CH:38]=[CH:37][C:29]([CH2:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][CH:31]2[CH2:32][CH2:33][N:34]([CH2:13][CH2:12][O:11][C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2](=[O:1])[CH2:10]4)[CH2:35][CH2:36]2)=[CH:37][CH:38]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 36998414-(4-Fluoro-benzyl)-piperidineHCID 54323087HCID 54323087, Verbindung

Produkt 1

HCID 232942774-(4-Fluorobenzyl)-1-(2-(2-oxo-1,3-dihydroindol-5-oxy)ethyl)piperidineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of toluene-4-sulfonic acid 2-(2-oxo-2,3-dihydro-1H-indol-5-yloxy)-ethyl ester (0.77 g, 2.22 mmol), 4-(4-fluorobenzyl)piperidine (1.1 g, 5.63 mmol), and potassium carbonate (2.2 g, 15.92 mmol) in acetonitrile (75 ml) was refluxed overnight under argon. The reaction mixture was cooled to room temperature and the solid was filtered off and washed with THF (3×20 ml). The filtrate was evaporated, and the solid chromatographed on silica gel eluting with 35% methanol/ethyl acetate to give the title compound (0.62 g, 76%) as a solid, mp 149-150° C. Analysis calculated for C22H25FN2O2 ·0.14H2O: C, 71.21; H, 6.87; N, 7.55; F, 5.12. Found: C, 71.21; H, 6.68; N, 7.49; F, 5.26.

Aufarbeitung

  1. temperaturewas refluxed overnight under argon
  2. filtrationthe solid was filtered off
  3. washwashed with THF (3×20 ml)
  4. customThe filtrate was evaporated
  5. customthe solid chromatographed on silica gel eluting with 35% methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-864d5909d54c406ea7497077cc0e6f41
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124323

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