1,4-Oxathian-2-one → N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-2-(2-hydroxyethylthio)acetamide

HRID 52097

Reaktionsgleichung

Reaktionsgleichung von HRID 52097
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:19]1[CH2:24][CH2:23][S:22][CH2:21][C:20]1=[O:25]>C(O)C>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][NH:18][C:20](=[O:25])[CH2:21][S:22][CH2:23][CH2:24][OH:19])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 3510601,4-Oxathian-2-oneHCID 146251023-({4-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amine

Produkt 1

HCID 19962907N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-2-(2-hydroxyethylthio)acetamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 0.38 g of 3-(4-piperidinomethyl-2-pyridyloxy)propylamine and 0.18 g of 1,4-oxathian-2-one was added to 10 ml of ethanol, and the resulting mixture was heated under reflux for 2 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure. The concentrate was mixed with water, and the resulting aqueous mixture was extracted with ethyl acetate. The extract was concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 1:9 by volume mixture of methanol and methylene chloride as the eluent, to give 0.49 g (yield 88%) of the title compound as an oil.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  4. additionThe concentrate was mixed with water
  5. extractionthe resulting aqueous mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated by evaporation under reduced pressure
  7. customthe concentrate was purified by column chromatography through silica gel
  8. additionby volume mixture of methanol and methylene chloride as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-6d43970eb09d4df986664b94bf5d6cb2
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616579

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