N-Phenylisonicotinamide → N-Phenyl-4-piperidinecarboxamide

HRID 1389151

Reaktionsgleichung

Reaktionsgleichung von HRID 1389151
[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Pt]=O>[C:1]1([NH:7][C:8]([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 1

HCID 220840N-Phenylisonicotinamide

Produkt 1

HCID 590499N-Phenyl-4-piperidinecarboxamideAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

4-(N-phenylcarbamoyl)pyridine [75.0 g, prepared as in Chem. Abs., 2013h (1958)] was hydrogenated in acetic acid (800 ml) using a platinum oxide catalyst at 50 p.s.i./30°. The catalyst was then removed by filtration, the solution evaporated, the residue basified to about pH 12 with sodium hydroxide, extracted with chloroform, and the organic extract discarded. The aqueous phase was evaporated to dryness, the residue boiled with chloroform, filtered and evaporated to leave 4-(N-phenylcarbamoyl)piperidine (17.0 g), m.p. 121°-127°. The hydrochloride salt, m.p. 231°-233°, was prepared in isopropanol from the free base and hydrogen chloride, and was recrystallised from isopropanol/ethyl acetate.

Aufarbeitung

  1. custom30°
  2. customThe catalyst was then removed by filtration
  3. customthe solution evaporated
  4. extractionextracted with chloroform
  5. extractionthe organic extract
  6. customThe aqueous phase was evaporated to dryness
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ed91d820945c4c76a1e29bdf3346ec42
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04243666

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