Water → HCID 18517197, compound

Temperature

-20 °C

To 18.11 g (100 mmoles) of 6-bromo-1-hexanol and 11.22 g (100 mmoles) of DABCO in 100 ml of anhydrous THF at −20° C., there is slowly added 19.06 g (100 mmoles) of tosyl chloride. After 24 hours under stirring at −20° C., the reaction mixture was filtered to remove the precipitate of DABCO hydrochloride. After evaporation of the solvent, a quantitative amount of 6-bromo-1-hexanol tosylate CH3FSO2O(CH2)6Br was recovered. This compound was thereafter dissolved in 20 ml of THF with 40 g of aniline FNH2 (200 mmoles) and this solution was heated to reflux overnight. After cooling, 300 ml of water were added and the organic phase was extracted with ether. After washing with water, the ether phase was dried with magnesium sulfate. After evaporation and drying, 23 g of N-(6-bromohexyl)aniline was obtained.

1. customat −20° C.
2. filtrationthe reaction mixture was filtered
3. customto remove the precipitate of DABCO hydrochloride
4. customAfter evaporation of the solvent
5. customa quantitative amount of 6-bromo-1-hexanol tosylate CH3FSO2O(CH2)6Br was recovered
6. temperaturethis solution was heated
7. temperatureto reflux overnight
8. temperatureAfter cooling
9. extractionthe organic phase was extracted with ether
10. washAfter washing with water
11. dry with materialthe ether phase was dried with magnesium sulfate
12. customAfter evaporation
13. customdrying

ORD record

ord-7ae7c1aae1214a699d8e710e83f41f59

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06333425B1