Ammonium formate → 4-Benzo[1,3]dioxol-4-yl-piperidine

HRID 1909357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909357
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)[C:5]=2[O:4][CH2:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:5]=2[O:4][CH2:3]1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 706564464-(Benzo[1,3]dioxol-4-yl)-1,2,3,6-tetrahydropyridine hydrochloride

Produkt 1

HCID 706572904-Benzo[1,3]dioxol-4-yl-piperidineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Pd/C 10% (169 mg, 159 μmol,) was added to a solution of 4-(benzo[1,3]dioxol-4-yl)-1,2,3,6-tetrahydropyridine hydrochloride (760 mg, 3.17 mmol) and ammonium formate (1.00 g, 15.9 mmol) in methanol (28.8 ml) under argon. After refluxing for 60 min the reaction mixture was cooled to room temperature, filtrated and concentrated under reduced pressure. Saturated sodium bicarbonate solution was added to the residue and the mixture was extracted with dichloromethane (3×25 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to yield the title compound as a white solid (0.654 grs, 100%). MS (ISP) m/z=206.0[(M+H)+].

Aufarbeitung

  1. temperatureAfter refluxing for 60 min the reaction mixture
  2. filtrationfiltrated
  3. concentrationconcentrated under reduced pressure
  4. additionSaturated sodium bicarbonate solution was added to the residue
  5. extractionthe mixture was extracted with dichloromethane (3×25 mL)
  6. dry with materialThe organic layers were dried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ae532a8722ee49fe9ab6be0c258bebc9
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598357B2

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