Reaktion #5188

Reaktionsgleichung

sodium chloride

sodium hydride

4-methoxybenzyl mercaptan

4-methanesulfonyloxy-1-methylpiperidine

→

title compound

4-(4-methoxybenzylthio)-1-methylpiperidine

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.WAITto stand overnight at room temperature
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   ExtraktionThe extract
5. 5
   Waschenas washed with an aqueous solution of sodium chloride
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   SonstigeThe solvent was then removed by distillation under reduced pressure
8. 8
   Sonstigethe residue was purified by column chromatography through silica gel (
9. 9
   Wascheneluted with a 1:4 by volume mixture of ethyl acetate and methanol)

Vorschrift

10.9 ml of 4-methoxybenzyl mercaptan were dissolved in 55 ml of dry dimethylformamide, and 3.4 g of sodium hydride (as a 55% w/w suspension in mineral oil) were added to the solution, whilst ice-cooling. The mixture was then stirred at room temperature for 30 minutes. At the end of this time, a solution of 12.6 g of 4-methanesulfonyloxy-1-methylpiperidine in 63 ml of dry dimethylformamide was added to the mixture, which was then allowed to stand overnight at room temperature. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract as washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 1:4 by volume mixture of ethyl acetate and methanol) to afford 9.01 g of the title compound as an oil.

Quelle