Triethylamine → 2-[3-(4-chlorophenyl)propyl]-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

Mesyl chloride (2.10 ml, 27.1 mmol) was added to a solution of 3-(4-chlorophenyl)propyl alcohol (4.6 g, 27 mmol) obtained in 1) above and triethylamine (3.78 ml, 27.1 mmol) in tetrahydrofuran (100 ml) at 0° C. and stirred at room temperature for 30 minutes. Water was added to the reaction mixture which was then extracted with ethyl acetate. The extract was washed with an aqueous saturated NaCl solution and dried over anhydrous magnesium sulfate. After the solvent was distilled away under reduced pressure, the reaction mixture and potassium phthalimide (5.02 g, 27.1 mmol) were dissolved in dimethylformamide and heated at 80° C. for 10 hours under stirring. 8 N aqueous sodium hydroxide was added to the resultant solution which was then extracted with ethyl acetate. The extract was washed with an aqueous saturated NaCl solution and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, whereby 7.47 g 2-[3-(4-chlorophenyl)propyl]-1H-isoindole-1,3(2H)-dione was obtained as solid.

Provenance & Evidence