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

Potassium carbonate (161.2 g) and potassium iodide (5 g) were added to the mixture of 1,3-dichloropropene (97.3 g) and (R)-1-(1-naphthyl)ethylamine (100 g) in isopropyl alcohol (500 mL) at room temperature. The reaction mixture was refluxed at 80° C. to 85° C. for about 4 hours. After the completion of the reaction, mixture was cooled to room temperature and filtered through hyflo bed. Hyflo bed was washed with isopropyl alcohol (500 mL). The filtrate was combined and treated with hydrochloric acid (6 Normal; 100 mL) at room temperature. The solution was allowed to stir for about one hour at room temperature to give solid. The solid was filtered and was washed twice with isopropyl alcohol (2×100 mL). Methanol (750 mL) was added to the wet solid and stirred for 10-15 minutes at room temperature. The pH of solution was adjusted to 11 to 12 using a solution of sodium hydroxide in water (20%). The solution was diluted with de-ionized water (750 mL) and extracted with dichloromethane (500 mL). Layers were separated and the organic layer was washed twice with de-ionized water (2×500 mL). The organic layer was completely concentrated under vacuum at 40° C. to 45° C. to give 3-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amine as oil.

1. temperatureThe reaction mixture was refluxed at 80° C. to 85° C. for about 4 hours
2. customAfter the completion of the reaction, mixture
3. filtrationfiltered through hyflo bed
4. washHyflo bed was washed with isopropyl alcohol (500 mL)
5. additiontreated with hydrochloric acid (6 Normal; 100 mL) at room temperature
6. customto give solid
7. filtrationThe solid was filtered
8. washwas washed twice with isopropyl alcohol (2×100 mL)
9. additionMethanol (750 mL) was added to the wet solid
10. stirringstirred for 10-15 minutes at room temperature
11. additionThe solution was diluted with de-ionized water (750 mL)
12. extractionextracted with dichloromethane (500 mL)
13. customLayers were separated
14. washthe organic layer was washed twice with de-ionized water (2×500 mL)
15. concentrationThe organic layer was completely concentrated under vacuum at 40° C. to 45° C.

ORD-Eintrag

ord-43f20897b98242b6b3c9e7482160aafd

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08759586B2