(Diethylamino)sulfur trifluoride → HCID 58772512, Verbindung

HRID 1361513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361513
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(S(F)(F)[F:30])CC.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])([F:30])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 58772035HCID 58772035, Verbindung

Produkt 1

HCID 58772512HCID 58772512, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-piperidin-4-ol (4b, 17 g, 0.05 mol) in dry dichloromethane (70 mL) was added dropwise DAST (10 g, 0.061 mol) at −78° C. under N2 atmosphere. The mixture was stirred at this temperature for 1 h and then warmed to room temperature slowly. NaHCO3 (sat., aq., 200 mL) was carefully added dropwise to quench the reaction. The separated aqueous was extracted with dichloromethane (150 mL×3), the combined extracts was washed with water and brine, dried over Na2SO4, concentrated to dryness. The residue was titrated with petroleum ether and the precipitated solid was filtered and washed with petroleum ether to afford 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-4-fluoro-piperidine 4c as white powder.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionThe separated aqueous was extracted with dichloromethane (150 mL×3)
  4. washthe combined extracts was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. filtrationthe precipitated solid was filtered
  8. washwashed with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-408901eeffa843a889637d75447e0294
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880007B2

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