Reacción #5598

Ecuación de reacción

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

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathen refluxed for 72 hours
2. 2
   FiltraciónThe hot mixture was filtered
3. 3
   Otrothe solvent removed on a rotary evaporator
4. 4
   OtroThe residue was triturated with hexane
5. 5
   workup.DISSOLUTIONdissolved in hot ethyl acetate
6. 6
   Temperaturato cool
7. 7
   FiltraciónAfter filtering
8. 8
   Otrothe solvent was removed by a rotary evaporator
9. 9
   Otrothe residue recrystallized from ethyl acetate-methanol-ethyl ether
10. 10
    Otroto give a tan solid

Procedimiento

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.

Fuente