Water → Quinoline

A mixture of phenethylamine (5.0 g), 5,6,7,8-tetrahydro-2-(phenylmethoxy)-5-oxoquinoline (10.0 g), and a catalytic amount of para-toluenesulfonic acid (206 mg) was heated under reflux in toluene (200 ml) with azeotropic removal of water for 36 hrs. The solution was cooled and washed with water. The aqueous phase was extracted with dichloromethane, and the combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. Sodium borohydride (1.4 g) was added to a solution of the residue and ethyl alcohol (125 ml) and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was concentrated in vacuo, the residue was quenched with water, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to afford 12.5 g (92%) of 5,6,7,8-tetrahydro-5-(2-phenethylamino)-2-phenylmethoxy)quinoline.

1. temperatureThe solution was cooled
2. washwashed with water
3. extractionThe aqueous phase was extracted with dichloromethane
4. washthe combined organic layers were washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. additionSodium borohydride (1.4 g) was added to a solution of the residue and ethyl alcohol (125 ml)
9. concentrationThe reaction mixture was concentrated in vacuo
10. customthe residue was quenched with water
11. extractionthe mixture was extracted with ethyl acetate
12. washThe combined organic layers were washed with brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationfiltered
15. concentrationthe filtrate was concentrated

ORD record

ord-d50902083cf7478bb4aa632c0ff196ad

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05310914