Reacción #96203

Ecuación de reacción

4-tert-Butyl-1-(prop-2-ynyl)piperidine

diethylamine

3,5-bistrifluoromethylbromobenzene

hydrogen chloride

→

1-(3,5-bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne hydrochloride

Disolventes

diethyl ether

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   Otrothus obtained
3. 3
   TemperaturaThe reaction mixture was heated
4. 4
   Temperaturaunder reflux for 17 hours
5. 5
   Temperaturacooled
6. 6
   Filtraciónfiltered
7. 7
   OtroThe filtrate was evaporated under reduced pressure (water-pump)
8. 8
   Otrothe residual oil thus obtained
9. 9
   workup.STIRRINGwith stirring, to the ethereal solution
10. 10
    FiltraciónThe resulting suspension was filtered
11. 11
    Lavadothe solid residue was washed with diethyl ether
12. 12
    Otrodried under vacuum

Procedimiento

4-tert-Butyl-1-(prop-2-ynyl)piperidine (prepared as described in Example 3; 37.3 g) and anhydrous diethylamine (800 ml) were added to 3,5-bistrifluoromethylbromobenzene [which may be prepared as described by E. T. McBee et al, J. Amer. Chem. Soc. (1950), 72, 1651; 61.0 g] and dichlorobis(triphenylphosphine)palladium (0.26 g), copper (I) iodide (0.26 g) and triphenylphosphine (0.26 g) were added with stirring, under an inert atmosphere, to the solution thus obtained. The reaction mixture was heated under reflux for 17 hours and then cooled and filtered. The filtrate was evaporated under reduced pressure (water-pump) and the residual oil thus obtained was dissolved in diethyl ether. A slight excess of a saturated solution of hydrogen chloride in anhydrous diethyl ether was then added, with stirring, to the ethereal solution. The resulting suspension was filtered and the solid residue was washed with diethyl ether and dried under vacuum, to give solid 1-(3,5-bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne hydrochloride (72 g), which was then partitioned between a small excess of 2 N aqueous sodium hydroxide solution and diethyl ether. The ethereal layer was dried over anhydrous sodium sulphate and evaporated, to give 1-(3,5-bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne in the form of an oil, which had the elementary analysis C: 61.7%; H: 5.8%; N: 3.5% (C20H23F6N requires C: 61.4%; H: 5.9%; N: 3.6%).

Fuente