Potassium Hydroxide → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(2-pyrimidinylthio) butyramide

HRID 52076

Reaktionsgleichung

Reaktionsgleichung von HRID 52076
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[K+].[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:34])[CH2:30][CH2:31][CH2:32]Cl)[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CO>[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:34])[CH2:30][CH2:31][CH2:32][S:1][C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 67726214N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-chlorobutyramideHCID 178418793HCID 178418793, Verbindung

Produkt 1

HCID 44211247N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(2-pyrimidinylthio) butyramideAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2.78 g of 2-mercaptopyrimidine were added to a solution of 1.95 g of 85% potassium hydroxide and 9.03 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-chlorobutyramide (prepared as described in Preparation 2) in 140 ml of methanol, and the resulting mixture was heated under reflux for 15 hours. At the end of this time, the reaction mixture was cooled, and the solvent was removed by distillation under reduced pressure. The resulting residue was mixed with water, and the 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 9:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 10.1 g (yield 92%) of the title compound as an oil.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 15 hours
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. customthe solvent was removed by distillation under reduced pressure
  5. additionThe resulting residue was mixed with water
  6. extractionthe aqueous mixture was extracted with ethyl acetate
  7. concentrationThe extract was concentrated by evaporation under reduced pressure
  8. customthe concentrate was purified by column chromatography through silica gel
  9. additionby volume mixture of ethyl acetate and methanol as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-6720e96c746444a589f225034fd47ddf
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616579

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