Reaction #6884

Reaction equation

2-iodotoluene

N-(2-propynyl)piperidine

→

oil

Yield 62.3%

1-(3-o-Tolyl-2-propynyl)piperidine

Yield 62.3%

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
   Concentrationconcentrated completely under reduced pressure
7. 7
   workup.DISTILLATIONDistillation of the residue under reduced pressure

Procedure

A mixture of 2-iodotoluene (6.54 g), N-(2-propynyl)piperidine (3.69 g), dichlorobis(triphenylphosphino)palladium(II) (0.05 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 concentrated completely under reduced pressure. Distillation of the residue under reduced pressure gave 3.98 g of an oil of boiling point 96–98° C./0.08 mm Hg.

Source