Reacción #2320112

Ecuación de reacción

5-Bromo-2-chlorobenzotrifluoride

1-benzyl-4-piperidone

→

title compound

Rendimiento 64.0%

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

Rendimiento 64.0%

Disolventes

diethyl ether

diethyl ether

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction gave rise to a solution of Grignard's reagent
2. 2
   Otrofinally quenched with saturated ammonium chloride solution (40 ml)
3. 3
   ExtracciónThe mixture was extracted several times with EtOAc
4. 4
   Secadothe combined organic phases were dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated to dryness

Procedimiento

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).

Fuente