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

HRID 1617314

Reaktionsgleichung

Reaktionsgleichung von HRID 1617314
[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-3e63012b4679453eb9937d612c2d2af2
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765959B2

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