Potassium Carbonate → Tert-butyl 4-[3-fluoro(4-fluorobenzyl)anilino]-1-piperidinecarboxylate

HRID 1724666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724666
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[N:5]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:8][CH2:7]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 23137591tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate

Produkt 1

HCID 9978463Tert-butyl 4-[3-fluoro(4-fluorobenzyl)anilino]-1-piperidinecarboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Tert-butyl 4-(3-fluoroanilino)-1-piperidinecarboxylate 1 (20 g) was dissolved in acetonitrile (250 ml). Potassium carbonate (33.2 g) and 1-(bromomethyl)-4-fluorobenzene (11 ml) were added to the solution. The reaction mixture was heated at reflux overnight, then cooled, concentrated and the residue was taken up in dichloromethane and water. The aqueous layer was washed twice with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated. The resulting white solid was triturated in hexane and filtered off to afford tert-butyl 4-[3-fluoro(4-fluorobenzyl)anilino]-1-piperidinecarboxylate 8 (25.5 g).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. concentrationconcentrated
  5. washThe aqueous layer was washed twice with dichloromethane
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. customThe resulting white solid was triturated in hexane
  9. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-7c978580178a4efaaef486768faac47a
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488741B2

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