Реакция #2320112

Уравнение реакции

5-Bromo-2-chlorobenzotrifluoride

1-benzyl-4-piperidone

→

title compound

Выход 64.0%

1-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-piperidine-4-ol

Выход 64.0%

Растворители

diethyl ether

diethyl ether

diethyl ether

Условия реакции

Обработка

1. 1
   ДругоеThe reaction gave rise to a solution of Grignard's reagent
2. 2
   Другоеfinally quenched with saturated ammonium chloride solution (40 ml)
3. 3
   ЭкстракцияThe mixture was extracted several times with EtOAc
4. 4
   Сушкаthe combined organic phases were dried (MgSO4)
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated to dryness

Методика

A solution of 5-Bromo-2-chlorobenzotrifluoride (5 g, 19.2 mmol) in dry diethyl ether (40 ml) was added dropwise at room temperature to a mixture of Mg (470 mg) in dry diethyl ether (20 ml) under a stream of Argon (g). The reaction gave rise to a solution of Grignard's reagent. A solution of 1-benzyl-4-piperidone (1.3 g, 6.88 mmol) in dry diethyl ether (30 ml) was added dropwise via syringe at room temperature. The combined mixture was stirred for 1 hour, and finally quenched with saturated ammonium chloride solution (40 ml). The mixture was extracted several times with EtOAc and the combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The oily residue was chromathographed on a silica column using EtOAc:toluene (1:1 (v/v)) as eluent affording the title compound (1.6 g, 64%). MS m/z (relative intensity, 70 eV) 369 (M+, 23), 278 (15), 91 (bp), 65 (16), 56 (21).

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