Reaktion #96203

Reaktionsgleichung

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

Lösungsmittel

diethyl ether

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Sonstigethus obtained
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturunder reflux for 17 hours
5. 5
   Temperaturcooled
6. 6
   Filtrationfiltered
7. 7
   SonstigeThe filtrate was evaporated under reduced pressure (water-pump)
8. 8
   Sonstigethe residual oil thus obtained
9. 9
   workup.STIRRINGwith stirring, to the ethereal solution
10. 10
    FiltrationThe resulting suspension was filtered
11. 11
    Waschenthe solid residue was washed with diethyl ether
12. 12
    Sonstigedried under vacuum

Vorschrift

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%).

Quelle