Water → HCID 18409092, compound

Temperature

0 °C

5,6,7,8-Tetrahydro-N,5-dimethyl-N,2-bis(phenylmethoxy)-5-quinolinamine (12.3 g) in tetrahydrofuran (160 ml) at 0° C. was treated dropwise with borane-tetrahydrofuran complex (1M in tetrahydrofuran, 63.4 ml). The solution was heated under reflux for 3 hrs., cooled to 0° C., and water (30 ml) was added. The reaction mixture was concentrated in vacuo, 20% potassium hydroxide solution (60 ml) was added, and the mixture was heated at reflux for 2 hrs. The mixture was cooled, acidified with conc hydrochloric acid, and washed with diethyl ether. The aqueous phase was basified with 20% potassium hydroxide solution and extracted with dichloromethane. The combined organic layers were washed with brine, dried over potassium carbonate, filtered, and the filtrate was concentrated to afford 6.3 g (92%) of product.

1. temperatureThe solution was heated
2. temperatureunder reflux for 3 hrs
3. concentrationThe reaction mixture was concentrated in vacuo, 20% potassium hydroxide solution (60 ml)
4. additionwas added
5. temperaturethe mixture was heated
6. temperatureat reflux for 2 hrs
7. temperatureThe mixture was cooled
8. washwashed with diethyl ether
9. extractionextracted with dichloromethane
10. washThe combined organic layers were washed with brine
11. dry with materialdried over potassium carbonate
12. filtrationfiltered
13. concentrationthe filtrate was concentrated

ORD record

ord-9b2bc3a09aff49bdb72131e4da56e825

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05216164