Reaction #6887

Reaction equation

propargyl bromide

4-methylpiperidine

potassium carbonate

→

oil

Yield 92.0%

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

Yield 92.0%

Solvents

acetone

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   ConcentrationThe filtrate was concentrated under reduced pressure
3. 3
   WashThe organic phase was washed with water (3×15 ml)
4. 4
   Dryingdried with sodium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   workup.DISTILLATIONDistillation of the residue under reduced pressure

Procedure

At 0–5° C., propargyl bromide (12.01 g) was added dropwise with stirring to a suspension of 4-methylpiperidine (10.0 g) and potassium carbonate (13.96 g) in dry acetone (80 ml). The mixture was stirred at 50° C. for 6 hours and then filtered. The filtrate was concentrated under reduced pressure and the residue was taken up in dichloromethane. The organic phase was washed with water (3×15 ml), dried with sodium sulfate and concentrated under reduced pressure. Distillation of the residue under reduced pressure gave 12.73 g of an oil of boiling point 60° C./16 mm Hg.

Source