N,N'-Dimethylethylenediamine → 1-[4-(Aminomethyl)phenyl]piperidin-2-one

HRID 1009468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009468
P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.I[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C:25]1=[O:30]>[Cu](I)I.C1(C)C=CC=CC=1>[NH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]2=[O:30])=[CH:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 126652-PiperidoneHCID 62657Potassium Phosphate, TribasicHCID 27375334-Iodobenzylamine

Produkt 1

HCID 47120251-[4-(Aminomethyl)phenyl]piperidin-2-oneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 41 mg of copper iodide, 1.82 g of tripotassium phosphate, 38 mg of N,N′-dimethylethylenediamine, 1.00 g of 1-(4-iodophenyl)methyl amine, and 510 mg of 2-piperidone was added 4.29 mL of toluene, followed by stirring at 80° C. overnight under an argon atmosphere. The reaction liquid was filtered through Celite, the filtrate was then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 552 mg of 1-[4-(aminomethyl)phenyl]piperidine-2-one.

Aufarbeitung

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. concentrationthe filtrate was then concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-7629a09261744cf381eb482db56278fe
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973078B2

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