Reacción #94953

Ecuación de reacción

ammonium chloride

water

4-bromobenzonitrile

4-chloro-1-methylpiperidine

magnesium

→

(4-bromophenyl)-(1-methyl-4-piperidinyl)methanone

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled (10°-15° C.) Grignard-complex
2. 2
   Otropreviously prepared
3. 3
   workup.STIRRINGUpon completion, stirring
4. 4
   Temperaturaat reflux temperature
5. 5
   ExtracciónThe product is extracted with methylbenzene
6. 6
   OtroThe extract is dried
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated
9. 9
   OtroThe residue is purified by column-chromatography over silica gel using
10. 10
    workup.ADDITIONa mixture of trichloromethane and methanol (95:5 by volume) as eluent
11. 11
    OtroThe pure fractions are collected
12. 12
    Otrothe eluent is evaporated

Procedimiento

To a stirred and cooled (10°-15° C.) Grignard-complex, previously prepared starting from 13.5 parts of 4-chloro-1-methylpiperidine and 2.4 parts of magnesium in 68 parts of tetrahydrofuran, is added dropwise a solution of 10 parts of 4-bromobenzonitrile in 22 parts of tetrahydrofuran. Upon completion, stirring is continued for 1 hour at reflux temperature. The reaction mixture is decomposed by pouring onto a mixture of 50 parts of ammonium chloride in 250 parts of water. The product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 10 parts of (4-bromophenyl)-(1-methyl-4-piperidinyl)methanone as a residue.

Fuente