Réaction #73828

Équation de réaction

4-(4-chloro-phenyl)-4-(4-iodo-phenyl)-piperidine

copper (I) cyanide

→

title compound

Rendement 16.0%

4-[4-(4-Chloro-phenyl)-piperidin-4-yl]-benzonitrile

Rendement 16.0%

Solvants

ethyl acetate

DMF

Conditions de réaction

Traitement

1. 1
   Températureto cool
2. 2
   Lavagewashed with a mixture of conc. ammonia and brine (×5)
3. 3
   Séchagedried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   Autreto give a residue which
7. 7
   Autrewas partially purified by column chromatography (SiO2)
8. 8
   Lavageeluting with a gradient of 2M ammonia in methanol (5% to 10%) and dichloromethane

Mode opératoire

A mixture of 4-(4-chloro-phenyl)-4-(4-iodo-phenyl)-piperidine and copper (I) cyanide in DMF was heated at 140° C. under nitrogen for 6 hours then allowed to cool. The mixture was diluted with ethyl acetate, washed with a mixture of conc. ammonia and brine (×5), dried (MgSO4), filtered and concentrated to give a residue which was partially purified by column chromatography (SiO2), eluting with a gradient of 2M ammonia in methanol (5% to 10%) and dichloromethane to afford the title compound (46 mg, <16%). This was taken on to the next reaction without further purification. LCMS (PS-A2) Rt 2.39 min [M+H]+ 297.

Source