Sodium hydride → HCID 13825040, Verbindung

HRID 648503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 648503
[H-].[Na+].Cl[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5]1.[SH:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1>CN(C)C=O>[N:23]1[CH:24]=[CH:25][C:20]([S:19][CH:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:11])[CH2:6][CH2:5]2)=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 13825039HCID 13825039, VerbindungHCID 178418431pyridine-4-thiol

Produkt 1

HCID 13825040HCID 13825040, VerbindungAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

60% Sodium hydride dispersion in a mineral oil (2.40 g) was slowly added to an ice-cooled solution of phenyl 4-chloro-1-piperidine-carboxylate (15.2 g) and 4-mercaptopyridine (6.66 g) in dry N,N-dimethylformamide (150 ml) with stirring under nitrogen gas. The mixture was stirred at the same temperature for 30 minutes and then at 80° C. for 4.5 hours. The resultant reaction mixture was poured into ice-water and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate, and concentrated to dryness in vacuo. The crystalline residue was recrystallized from a mixture of n-hexane and isopropanol to give phenyl 4-[(4-pyridyl)thio]-1-piperidine-carboxylate (15.4 g) as colourless crystals.

Aufarbeitung

  1. stirringThe mixture was stirred at the same temperature for 30 minutes
  2. customThe resultant reaction mixture
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness in vacuo
  7. customThe crystalline residue was recrystallized from a mixture of n-hexane and isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-55e096191cbf498fa9dbc524d63042ae
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04735952

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