Water → 1-(3,4-Dimethoxy-phenyl)-piperidine-4-one

HRID 2245344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245344
[I-].C([N+]1(C)[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)C1C=CC=CC=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[NH2:22].C(=O)([O-])[O-].[K+].[K+].O>C(O)C.C(=O)([O-])[O-].[K+].[K+]>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([N:22]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Komponenten

7

Edukt 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 227703,4-DimethoxyanilineHCID 110780641-Benzyl-1-methyl-4-oxopiperidinium iodide

Produkt 1

HCID 220002541-(3,4-Dimethoxy-phenyl)-piperidine-4-oneAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11430Potassium CarbonateKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A slurry of 1-benzyl-1-methyl-4-oxo-piperidinium iodide (9270 mg), 3,4-dimethoxy aniline (3900 mg) and anhydrous potassium carbonate (437 mg) in ethanol (90 ml)/water (45 ml) were heated to reflux for 6 hours. Additional potassium carbonate (200 mg) was added and the reaction was heated to 100° C. over night. Water (50 ml) was added to the reaction mixture, which was extracted three times with DCM. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and the solvent was evaporated in vacuo to leave the crude product as a dark oil. The residue was purified by column chromatography (ethyl acetate/hexanes=1:1) to yield the product as a yellow solid (3700 mg). MS (ESI): 236.1 (MH+).

Aufarbeitung

  1. temperatureto reflux for 6 hours
  2. extractionwas extracted three times with DCM
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customto leave the crude product as a dark oil
  8. customThe residue was purified by column chromatography (ethyl acetate/hexanes=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d742b2973ace485ca544ba4a79fd708c
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683079B2

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