Benzoyl chloride → N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-benzoyloxyethylthio)acetamide

HRID 52054

Reaktionsgleichung

Reaktionsgleichung von HRID 52054
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:10]1([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([O:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][NH:28][C:29](=[O:35])[CH2:30][S:31][CH2:32][CH2:33][OH:34])[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>N1C=CC=CC=1>[N:10]1([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([O:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][NH:28][C:29](=[O:35])[CH2:30][S:31][CH2:32][CH2:33][O:34][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

4

Edukt 2

HCID 7412Benzoyl chlorideHCID 67725880N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-hydroxyethylthio)acetamide

Produkt 1

HCID 67725898N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-benzoyloxyethylthio)acetamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

0.24 ml of benzoyl chloride was added, whilst ice-cooling, to a mixture of 0.40 g of N-[4-(4-piperidinomethyl -2-pyridyloxy)-cis-2-butenyl]-2-(2-hydroxyethylthio)acetamide (prepared as described in Example 1) and 1.02 ml of pyridine, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the mixture was concentrated by evaporation under reduced pressure. The concentrate was diluted with water and made alkaline by the addition of an aqueous ammonia solution, after which it 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 1:40 by volume mixture of methanol and ethyl acetate as the eluent, to give 0.31 g of the title compound in a 61% yield.

Aufarbeitung

  1. concentrationAt the end of this time, the mixture was concentrated by evaporation under reduced pressure
  2. additionThe concentrate was diluted with water
  3. additionby the addition of an aqueous ammonia solution
  4. extractionafter which it was extracted with ethyl acetate
  5. concentrationThe extract was concentrated by evaporation under reduced pressure
  6. customthe concentrate was purified by column chromatography through silica gel
  7. additionby volume mixture of methanol and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-3359d1534e2248b0acdef42c9bd27b85
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616579

Verknüpfte Notizen

Wird geladen…