Cyclohexanone → N-(1-Cyclohexyl-piperidin-4-yl)-N-(4-fluoro-phenyl)-acetamide

HRID 507859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507859
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH:18]1([N:15]2[CH2:16][CH2:17][CH:12]([N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9](=[O:11])[CH3:10])[CH2:13][CH2:14]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 18539208HCID 18539208, Verbindung

Produkt 1

HCID 11951208N-(1-Cyclohexyl-piperidin-4-yl)-N-(4-fluoro-phenyl)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

N-(4-fluoro-phenyl)-N-piperidin-4-yl-acetamide (60 mg; 0.25 mmol; 1 eq.), see Example 6 for deprotection procedure, and cyclohexanone (29 mg; 0.30 mmol; 1.2 eq.) were dissolved in DCE (2 mL). NaBH(OAc)3 (108 mg; 0.51 mmol; 2 eq.) was added, and the reaction was stirred at room temperature for 72 hours and then quenched with 1N NaOH (5 mL). DCM (5 mL) was then added and the layers were separated. The aqueous layer was washed with DCM (10 mL) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified using reversed-phase HPLC (2-99% CH3CN/H2O gradient with 0.05% TFA). LC/MS M/Z 319.2, Retention time=1.88 minutes; 10-99% CH3CN/H2O gradient with 0.05% TFA.

Aufarbeitung

  1. customquenched with 1N NaOH (5 mL)
  2. additionDCM (5 mL) was then added
  3. customthe layers were separated
  4. washThe aqueous layer was washed with DCM (10 mL)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-bb8fe3bf796a4fbd91d29254726acbee
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786308B2

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