Reacción #54352

Ecuación de reacción

3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]piperidine

potassium carbonate

1-bromo-2-propyne

→

3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-(2-propynyl)piperidine

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONA mixture of 0.900 g
2. 2
   Temperaturaat reflux for 22 hours
3. 3
   OtroThe reaction mixture is then evaporated
4. 4
   workup.DISSOLUTIONdissolved in 100 ml
5. 5
   ExtracciónThe organic extract
6. 6
   Lavadois washed with two 150 ml
7. 7
   Secadoportions of saturated sodium chloride, dried over magnesium sulfate
8. 8
   Otroevaporated
9. 9
   OtroThe residue is purified via column chromatography on 100 g
10. 10
    Lavadosilica gel eluted with 2% methanol-dichloromethane
11. 11
    OtroThe product is crystallized from pentane (117 mg., 11.5%)

Procedimiento

A mixture of 0.900 g. (2.97 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]piperidine, 481 mg. (3.49 mmoles) of anhydrous potassium carbonate and 353 mg. (2.97 mmoles) of 1-bromo-2-propyne in 20 ml. of ethanol is heated at reflux for 22 hours. The reaction mixture is then evaporated and dissolved in 100 ml. of saturated sodium bicarbonate and 200 ml. of dichloromethane. The organic extract is washed with two 150 ml. portions of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 100 g. silica gel eluted with 2% methanol-dichloromethane. The product is crystallized from pentane (117 mg., 11.5%).

Fuente