تفاعل #1134569

معادلة التفاعل

1-bromo-4-trifluoromethyl-benzene

piperidin-4-ylmethyl-carbamic acid tert-butyl ester

cesium carbonate

2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

→

desired product

المردود 61.8%

[1-(4-trifluoromethyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester

المردود 61.8%

المذيبات

water

dioxane

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةmaintained at that temperature for 28 hr
2. 2
   درجة الحرارةto cool to room temperature
3. 3
   استخلاصextracted with dichloromethane (2×1 L)
4. 4
   تجفيفThe combined organic phases were dried over sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   أخرىthe solvents were removed under reduced pressure
7. 7
   workup.DISSOLUTIONThe resulting residue was dissolved in acetonitrile (1.5 L)
8. 8
   workup.ADDITIONWater (1.5 L) was then added
9. 9
   workup.STIRRINGwith stirring
10. 10
    ترشيحThis resulting in a precipitate, which was filtered
11. 11
    أخرىdried overnight at 40° C. at a pressure of 3 mbar

الإجراء التجريبي

A solution of 1-bromo-4-trifluoromethyl-benzene (50.0 g; 220 mmol) and piperidin-4-ylmethyl-carbamic acid tert-butyl ester (48.1 g; 220 mmol) in dioxane (1 L) was added to a suspension of palladium (II) acetate (7.41 g; 33 mmol), cesium carbonate (144.8 g; 440 mmol), and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (31.8 g; 45 mmol) in dioxane (1 L). The resulting mixture was heated to 110° C., and then maintained at that temperature for 28 hr with stirring. The mixture was then allowed to cool to room temperature. Afterward, the reaction mixture was treated with water (2 L) and extracted with dichloromethane (2×1 L). The combined organic phases were dried over sodium sulfate and filtered, and then the solvents were removed under reduced pressure. The resulting residue was dissolved in acetonitrile (1.5 L). Water (1.5 L) was then added with stirring. This resulting in a precipitate, which was filtered and then dried overnight at 40° C. at a pressure of 3 mbar to afford the desired product (48.9 g; 136 mmol).

المصدر