Reaction #6886

Reaction equation

3-fluoroiodobenzene

4-methyl-1-(2-propynyl)piperidine

→

oil

Yield 56.2%

1-[3-(3-Fluorophenyl)-2-propynyl]-4-methylpiperidine

Yield 56.2%

Solvents

diethylamine

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 5 hours
3. 3
   OtherThe solvent was removed under reduced pressure
4. 4
   Washwashed with water
5. 5
   DryingThe organic phase was dried over magnesium sulfate
6. 6
   Otherthe solvent was removed under reduced pressure
7. 7
   workup.DISTILLATIONDistillation of the residue under reduced pressure

Procedure

A mixture of 3-fluoroiodobenzene (8.88 g), 4-methyl-1-(2-propynyl)piperidine (6.80 g), palladium acetate (0.045 g), tri-o-toloylphosphine (0.24 g) and copper(I) iodide (0.1 g) in dry diethylamine (50 ml) was heated under reflux for 5 hours. The solvent was removed under reduced pressure and the residue was taken up in diethyl ether and washed with water. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. Distillation of the residue under reduced pressure gave an oil (5.20 g) of boiling point 105° C./0.07 mm Hg.

Source