Allyl bromide → HCID 21714433, compound

Temperature

5 °C

To a 500 mL 3-necked round-bottomed flask, was added 24.0 g of decahydroquinoline dissolved in 150 mL acetone. To this mixture was added 29.7 g of powdered anhydrous potassium carbonate. The reaction mixture was cooled to 5° C. with an ice bath. While stirring, 20.8 g of allyl bromide in 50 mL acetone was added slowly to the reaction mixture. After addition was complete, the reaction mixture was allowed to stir at room temperature for 24 hours. The reaction mixture was filtered, and the solvent was removed from the filtrate under reduced pressure using a rotary evaporator yielding 23.0 g of N-allyl decahydroquinoline as a viscous liquid. To a 500 mL 3-necked round-bottomed flask was added 22.0 g of N-allyl decahydroquinoline dissolved in 100 mL diethyl ether. After cooling to 5° C. with an ice bath, 15.5 g of allyl bromide in 20 mL 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 with diethyl ether (2×500 mL). The washed solid was recrystalled from acetonitrile. After removal of acetonitrile by filtration, the residue was dried under vacuum yielding 24.0 g of N,N-diallyl decahydroquinolinium bromide as a white solid.

1. additionAfter addition
2. stirringto stir at room temperature for 24 hours
3. filtrationThe reaction mixture was filtered
4. customthe solvent was removed from the filtrate under reduced pressure
5. customa rotary evaporator

ORD record

ord-455960ddb1774f609fe94b9156c24d3f

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06271264B1