Propargyl bromide → 4-Propargyl-4-azatricyclo[4.3.1.13,8]undecan-5-one

Temperature

90 °C

A solution of potassium hydroxide (0.56 gram, 10 mmol) in 3 ml of absolute methanol was added to 4-azatricyclo[4.3.1.13,8 ]undecan-5one (1.65 gram, 10 mmol) and the solvent was slowly removed under reduced pressure with the internal temperature not exceeding 25° C. When solid began to separate, anhydrous toluene was added and the solvent removal continued (a total of 30 ml of toluene were removed), then the temperature was raised to 90° C. (with the distillation continuing at atmospheric pressure--a total of 10 ml of toluene were distilled). The reaction mixture was cooled to 40° C. and propargyl bromide (0.9 ml, 10 mmol) was added dropwise. The temperature was raised to 65° C. and the mixture stirred for 4 hours. The solid precipitate was filtered off, and the filtrate was evaporated to yield 1.82 gram of compound 5a. Melting point 168°-170° C. (recrystallized from a petr. ether-ethanol 10:1 mixture by volume).

1. customthe solvent was slowly removed under reduced pressure with the internal temperature not
2. customexceeding 25° C
3. customto separate
4. additionanhydrous toluene was added
5. customthe solvent removal
6. customwere removed), then the temperature
7. distillationwith the distillation
8. distillationa total of 10 ml of toluene were distilled)
9. temperatureThe reaction mixture was cooled to 40° C.
10. temperatureThe temperature was raised to 65° C.
11. filtrationThe solid precipitate was filtered off
12. customthe filtrate was evaporated

ORD record

ord-05f33badeb484ab0ac9e1da55b31fe3d

Source dataset

uspto-grants-1985_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04557865