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

Potassium carbonate (161.2 g) and potassium iodide (5 g) were added to a solution of (R)-1(1-naphthyl)ethylamine (100 g) and 1,3-dichloropropene (97.3 g) in acetonitrile (1 L) at room temperature. The reaction mixture was refluxed at 80° C. to 85° C. for 4 hours. After the completion of the reaction, the mixture was cooled to room temperature and de-ionized water (500 mL) was added. The solution was stirred for 15 minutes and layers were separated. The organic layer was concentrated under vacuum at 55° C. to 60° C. till about 100 to 150 mL of residue was left. Toluene (500 mL) was added to the residue and the organic layer was washed twice with de-ionized water (2×250 mL). The organic layer was concentrated under vacuum at 55° C. to 60° C. Isopropyl alcohol was added to the residue and stirred for 10 minutes at room temperature. The pH of the solution was adjusted to 0.5 to 1.0 using concentrated hydrochloric acid (35 mL) and stirred for one hour at room temperature. The solid was filtered, washed with isopropyl alcohol (2×100 mL) and dried under vacuum at 45° C. to 50° C.

1. temperatureThe reaction mixture was refluxed at 80° C. to 85° C. for 4 hours
2. customAfter the completion of the reaction
3. customlayers were separated
4. concentrationThe organic layer was concentrated under vacuum at 55° C. to 60° C. till about 100 to 150 mL of residue
5. waitwas left
6. additionToluene (500 mL) was added to the residue
7. washthe organic layer was washed twice with de-ionized water (2×250 mL)
8. concentrationThe organic layer was concentrated under vacuum at 55° C. to 60° C
9. additionIsopropyl alcohol was added to the residue
10. stirringstirred for 10 minutes at room temperature
11. stirringstirred for one hour at room temperature
12. filtrationThe solid was filtered
13. washwashed with isopropyl alcohol (2×100 mL)
14. customdried under vacuum at 45° C. to 50° C.

ORDレコード

ord-d280ecfc7458440683e57b6c63168e3d

出典データセット

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08759586B2