Potassium Carbonate → 4-Acetamido-2-(6-phenoxy-2-pyridyl)piperidine

HRID 647510

Reaktionsgleichung

Reaktionsgleichung von HRID 647510
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:21]([NH:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)(=[O:23])[CH3:22]>S1(CCCC1)(=O)=O.[Cu]>[C:21]([NH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH:27]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:3]=2)[CH2:26]1)(=[O:23])[CH3:22]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 21288N-Pyridin-4-ylacetamideHCID 8176622-Chloro-6-phenoxypyridine

Produkt 1

HCID 204851724-Acetamido-2-(6-phenoxy-2-pyridyl)piperidineAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 31347SulfolaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 0.116 moles of 2-chloro-6-phenoxypyridine, 21.5 g of anhydrous potassium carbonate, 0.151 moles of 4-acetamidopyridine and 0.118 mole of copper in powder form in 100 ml of sulfolane is heated to 150° C. with stirring for 40 hours. The sulfolane is distilled, the residue is taken up with water, the suspension is treated with water and it is extracted with methylene chloride. The organic phase is washed with water, dried and concentrated to dryness. By crystallisation of the residue in diisopropylic ether, 4-acetamido-2-(6-phenoxy-2-pyridyl)piperidine is obtained; m.p. 104° to 106° C.

Aufarbeitung

  1. distillationThe sulfolane is distilled
  2. additionthe suspension is treated with water and it
  3. extractionis extracted with methylene chloride
  4. washThe organic phase is washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customBy crystallisation of the residue in diisopropylic ether

Quellen und Nachweise

ORD-Eintrag
ord-5bf9257e65124006800c87f38633ee38
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04409228

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