Réaction #5598

Équation de réaction

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

Solvants

acetonitrile

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source