Allyl bromide → 1-(2-Propenyl)piperidine

Temperature

5 °C

213 9 of piperidine dissolved in 300 mL of diethyl ether and was added to a 1 L 3-necked round-bottomed flask. The mixture was cooled to 5° C. with an ice bath. While stirring, a solution of 151.2 g of allyl bromide in 60 mL of diethyl ether was added slowly to the piperidine solution. After addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours. The white precipitate formed was removed by filtration. Ether was removed from the filtrate at room temperature using a rotary evaporator. The residual liquid was fractionally distilled yielding 108 g of N-allylpiperidine. To a 500 mL 3-necked round-bottomed flask was added 40.1 9 of N-allylpiperidine dissolved in 50 mL of diethyl either. After cooling to 5° C. with an ice bath, a solution of 38.7 g of allyl bromide in 30 mL of diethyl ether was added slowly. After completion of addition of allyl bromide the reaction mixture was allowed to warm to room temperature and stirred at room temperature for 24 hours. The solid residue thus formed was collected by filtration and was washed twice with 1.5 L of diethyl ether. The washed solid was dried under vacuum yielding 44 9 of N,N-diallylpiperidinium bromide as a white solid.

1. additionwas added to a 1 L 3-necked round-bottomed flask
2. additionAfter addition
3. stirringto stir at room temperature for 18 hours
4. customThe white precipitate formed
5. customwas removed by filtration
6. customEther was removed from the filtrate at room temperature
7. customa rotary evaporator
8. distillationThe residual liquid was fractionally distilled

ORD record

ord-a4b0134c0b6045c4b3b18545a59b68f0

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06271264B1