反応 #96203

反応方程式

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

溶媒

diethyl ether

diethyl ether

反応条件

後処理

1. 1
   workup.ADDITIONwere added
2. 2
   その他thus obtained
3. 3
   温度The reaction mixture was heated
4. 4
   温度under reflux for 17 hours
5. 5
   温度cooled
6. 6
   ろ過filtered
7. 7
   その他The filtrate was evaporated under reduced pressure (water-pump)
8. 8
   その他the residual oil thus obtained
9. 9
   workup.STIRRINGwith stirring, to the ethereal solution
10. 10
    ろ過The resulting suspension was filtered
11. 11
    洗浄the solid residue was washed with diethyl ether
12. 12
    その他dried under vacuum

実験手順

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%).

出典