Sodium Hydroxide → 1-Benzyl-4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine

HRID 1978831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978831
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([F: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.[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.CCOC(C)=O.O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 2

HCID 14798Sodium HydroxideHCID 15512819HCID 15512819, Verbindung2×

Produkt 1

HCID 155128201-Benzyl-4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridineAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1118Sulfuric AcidKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyl-4-(5-fluoro-2-methoxy-phenyl)-4-hydroxypiperidine (1.01 g, 3.20 mmole) (Intermediate 1) in acetic acid (40 mL) at room temperature was added 2 drops of concentrated sulfuric acid. The resulting solution was heated to reflux, and the mixture stirred for 2 days. The mixture was cooled to room temperature and diluted with EtOAc (100 mL) and water (100 mL). The solution was basified with 50% NaOH solution until pH=10. The layers were separated and the organics washed with brine. The combined aqueous layers were extracted three times with EtOAc (50 mL). The combined organic layers were dried over Na2SO4 and concentrated. Flash chromatography (elution with 1:1 EtOAc-hexane) to give 0.62 g (65%) of 1-benzyl-4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine as a yellow oil.

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. customThe layers were separated
  4. washthe organics washed with brine
  5. extractionThe combined aqueous layers were extracted three times with EtOAc (50 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. washFlash chromatography (elution with 1:1 EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1efab397ffbc4ab3b627dfd92d1e9432
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239126B1

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