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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence