Hydrochloric Acid → 3-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amine

Temperatur

40 °C

Potassium carbonate (72.5 g), Tetrabutyl ammonium bromide (30 g) and de-ionized water (75 mL) were added to (R)-1-(1-naphthyl)ethylamine (150 g) in toluene (750 mL) at room temperature. The reaction mixture was heated to 60° C. to 70° C. and added trans 1,3-dichloropropene (126.4 g). The reaction mass was refluxed for 3 hours at 90° C. to 95° C. The reaction mixture was cooled to 40° C., and washed with de-ionized water (2×450 mL). The organic layer was separated and concentrated under vacuum at 55° C. to 60° C. to give an oily residue. The residue was dissolved in acetone (750 mL), added de-ionized water (150 ml) and the pH of the reaction mixture was adjusted to 1-2 using aqueous hydrochloric acid (6 Normal; 150 mL). The solid was stirred at 30° C. to 40° C. for 30 min, cooled to 20° C. to 25° C. and stirred for 1 hour. The resulting solid was filtered and suspended in acetone (300 mL), the suspensions were filtered and washed with acetone (150 mL). The resulting solid was suspended in de-ionized water (300 mL), filtered and washed with de-ionized water (225 mL). The resulting wet solid was suspended in a mixture of toluene (750 mL), methanol (375 mL) and de-ionized water (375 mL). The pH of the mixture was adjusted to 11-11.5 using aqueous sodium hydroxide solution (20%; 150 mL) and stirred for 30 minutes. The layers were separated and organic layer was washed with de-ionized water (2×300 mL). The organic layer was concentrated under reduced pressure to give 3-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amine as an oil.

1. temperatureThe reaction mixture was heated to 60° C. to 70° C.
2. temperatureThe reaction mass was refluxed for 3 hours at 90° C. to 95° C
3. washwashed with de-ionized water (2×450 mL)
4. customThe organic layer was separated
5. concentrationconcentrated under vacuum at 55° C. to 60° C.
6. customto give an oily residue
7. temperaturecooled to 20° C. to 25° C.
8. stirringstirred for 1 hour
9. filtrationThe resulting solid was filtered
10. filtrationthe suspensions were filtered
11. washwashed with acetone (150 mL)
12. filtrationfiltered
13. washwashed with de-ionized water (225 mL)
14. additionThe resulting wet solid was suspended in a mixture of toluene (750 mL), methanol (375 mL) and de-ionized water (375 mL)
15. stirringstirred for 30 minutes
16. customThe layers were separated
17. washorganic layer was washed with de-ionized water (2×300 mL)
18. concentrationThe organic layer was concentrated under reduced pressure

ORD-Eintrag

ord-eef8dbce46964f63b5440278aed7b351

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08759586B2