Reaction #1062

Reaction equation

compound ( 4 )

4-(4-phenoxyphenyl)piperidine

chloroacetonitrile

sodium iodide

potassium carbonate

→

compound ( 26 )

Yield 91.0%

1-cyanomethyl-4-(4-phenoxyphenyl)piperidine

Yield 91.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   TemperatureThis was then heated
2. 2
   Temperatureat reflux for 2 hours
3. 3
   Extractionextraction
4. 4
   OtherThe extract was dried
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   Otherto obtain a residue which
8. 8
   Otherwas then purified by silica gel column chromatography (methylene chloride:methanol =30:1)

Procedure

To an 8 ml dimethylformamide solution of 300 mg of the compound (4) synthesized in Reference Example 4 were added 93 mg of chloroacetonitrile, 355 mg of sodium iodide, and 196 mg of potassium carbonate. This was then heated at reflux for 2 hours. To the reaction was added 10 ml of ice water, then extraction was performed with ethyl acetate. The extract was dried, filtered, then concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (methylene chloride:methanol =30:1) to obtain the above-identified compound (26) in an amount of 313 mg (yield of 91%).

Source