Reaktion #5598

Reaktionsgleichung

product

N-1-Azabicyclo[2.2.2]oct-3-yl-2-chloroacetamide, monohydrochloride

2,6-bis(1,1-dimethylethyl)-4-mercaptophenol

Triethylamine

→

title compound

N-1-Azabicyclo[2.2.2]oct-3-yl-2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]acetamide, monohydrochloride

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen refluxed for 72 hours
2. 2
   FiltrationThe hot mixture was filtered
3. 3
   Sonstigethe solvent removed on a rotary evaporator
4. 4
   SonstigeThe residue was triturated with hexane
5. 5
   workup.DISSOLUTIONdissolved in hot ethyl acetate
6. 6
   Temperaturto cool
7. 7
   FiltrationAfter filtering
8. 8
   Sonstigethe solvent was removed by a rotary evaporator
9. 9
   Sonstigethe residue recrystallized from ethyl acetate-methanol-ethyl ether
10. 10
    Sonstigeto give a tan solid

Vorschrift

The title compound was prepared by dissolving the product of Example 17 (2.0 g, 0.0084 mole) and 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (1.99 g, 0.0084 mole) in acetonitrile (25 ml). Triethylamine (5 ml) was added to the mixture and the mixture stirred at room temperature for 12 hours then refluxed for 72 hours. The hot mixture was filtered and the solvent removed on a rotary evaporator. The residue was triturated with hexane and dissolved in hot ethyl acetate and allowed to cool. After filtering, the solvent was removed by a rotary evaporator and the residue recrystallized from ethyl acetate-methanol-ethyl ether to give a tan solid. The structure was confirmed by mass spectroscopy M+ 404.

Quelle