4-Carbamoyl-1-phenyl-pyridinium hydrochloride → 1-Phenylpiperidine-4-carboxamide

HRID 2233285

Reaktionsgleichung

Reaktionsgleichung von HRID 2233285
Cl.[C:2]([C:5]1[CH:10]=[CH:9][N+:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])[NH2:3]>[Pd].C(O)C.CCO>[C:11]1([N:8]2[CH2:9][CH2:10][CH:5]([C:2]([NH2:3])=[O:4])[CH2:6][CH2:7]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

4

Edukt 1

HCID 686786254-Carbamoyl-1-phenyl-pyridinium hydrochloride

Produkt 1

HCID 105843391-Phenylpiperidine-4-carboxamideAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 57419690EtOH EthanolLösungsmittel

Versuchsvorschrift

2.0 g palladium on charcoal (10%) were added to a solution of 22.7 g 4-Carbamoyl-1-phenyl-pyridinium hydrochloride in 500 ml ethanol EtOH. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen at 3 bar for one hour. The catalyst was filtered off through a pad of celite and washed with ethanol. The filtrate was evaporated in vacuo. The resulting residue was purified by flash chromatography on silica gel with the eluent ethyl acetate:methanol=9:1=>4:1 to obtain 6.9 g 1-Phenyl-piperidine-4-carboxylic acid amide as a solid.

Aufarbeitung

  1. filtrationThe catalyst was filtered off through a pad of celite
  2. washwashed with ethanol
  3. customThe filtrate was evaporated in vacuo
  4. customThe resulting residue was purified by flash chromatography on silica gel with the eluent ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-89dece25bbe4465f8c61ac5c56ea27e6
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709481B2

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