4-(4-Ethoxyphenyl)pyridine → 4-(4-Ethoxyphenyl)piperidine

HRID 409734

Reaktionsgleichung

Reaktionsgleichung von HRID 409734
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)[CH3:2]>C(O)(=O)C.[Pt](=O)=O>[CH2:9]1[CH2:4][O:3][CH2:7][CH2:8]1.[CH3:1][OH:3].[NH4+:13].[OH-:3].[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[CH:6][CH:5]=1)[CH3:2]

Komponenten

5

Edukt 1

HCID 707009334-(4-Ethoxyphenyl)pyridine

Produkt 2

HCID 214951914-(4-Ethoxyphenyl)piperidineHCID 86686122THF MeOH NH4OH

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

410 mg (2.06 mmol) 4-(4-Ethoxy-phenyl)-pyridine in 10 mL acetic acid are hydrogenated (3 bar) for 9 h at rt using 50 mg platinum(IV) oxide. After that time, the catalyst is filtered off and the solvent is evaporated. The residue is taken up in 1N NaOH and extracted with EtOAc. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; DCM:MeOH 9:1, then THF:MeOH:NH4OH 1:1:0.1) to yield the desired product.

Aufarbeitung

  1. customfor 9 h
  2. customat rt
  3. filtrationAfter that time, the catalyst is filtered off
  4. customthe solvent is evaporated
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer is dried over sodium sulphate
  7. customthe solvent is evaporated
  8. customThe residue is purified by column chromatography (silica gel

Quellen und Nachweise

ORD-Eintrag
ord-db7752a720184053b3748059490b60bf
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759528B2

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