Propargyl bromide → 4-Tert-butyl-1-(prop-2-ynyl)piperidine

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Anhydrous potassium carbonate (196 g) was added to a solution of 4-tert-butylpiperidine (98.9 g) in anhydrous acetone (1.2 liters) and the resulting suspension was cooled to 0° C., with stirring under an inert atmosphere. A solution of 1-bromoprop-2-yne (87.5 g) in anhydrous acetone (100 ml) was then added dropwise, the temperature being maintained below 5° C. The reaction mixture was then stirred at ambient temperature for 24 hours, filtered and the filtrate was evaporated under reduced pressure (water-pump). The residual oil thus obtained was extracted with petroleum spirit (b.p. 40°-60° C.). The resulting solution was treated with decolourizing charcoal, filtered and the filtrate was evaporated to give 4-tert-butyl-1-(prop-2-ynyl)piperidine (105 g), m.p. 48°-49° C., which may be further purified by distillation under reduced pressure (water-pump) (b.p. 108°-110° C./15 mm Hg) or by sublimation under reduced pressure (water-pump) at 80° C./20 mm Hg.

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