Piperidine → 2-(1-Piperidinylcarbonyl)cyclohexanone

HRID 1629593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629593
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O:10]CC)=O.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[N:13]1([C:8]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]2=[O:1])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

4

Edukt 2

HCID 8082PiperidineHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Produkt 1

HCID 134131852-(1-Piperidinylcarbonyl)cyclohexanoneAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Ethyl 2-oxocyclohexane-carboxylate (5.3 g, 31 mmol, 5.0 mL) DMAP (1.05 g, 9.4 mmol) and piperidine (5.3 g, 63 mmol, 6.2 mL) in toluene (100 mL) were heated at reflux for 4 days. The reaction was allowed to cool and the reaction was concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (20-80% (B), 100 g, 8 CV, 85 mL/min) to afford 6.26 g (96%) of 2-(piperidine-1-carbonyl)-cyclohexanone (19) as a white solid. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 23.5, 24.5, 25.5, 26.2, 27.1, 30.4, 41.9, 42.9, 46.8, 54.2, 167.6, 207.6.

Aufarbeitung

  1. temperatureat reflux for 4 days
  2. temperatureto cool
  3. concentrationthe reaction was concentrated in vacuo
  4. customThe crude material was purified by silica gel chromatography
  5. washeluting with petrol (A) and ethyl acetate (B) (20-80% (B), 100 g, 8 CV, 85 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-d4164a5a41d54ef9b75bb42ec727bcd1
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08790619B2

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