Isopropylamine → Benzyl 3-(isopropylamino)benzoate

Participants

Reaction Conditions

Reaction Steps

Copper iodide (1.0 equiv) and cesium carbonate (2.0 equiv) were added to a microwave vial and the vial was evacuated and filled with argon three times. Benzyl 3-iodobenzoate (4) in dry dimethylformamide (2 M), isopropylamine (2.0 equiv) and 2-isobutyrylcyclohexanone (0.2 equiv) were then added to the vial, the vial was sealed and the resulting mixture is heated to 100° C. under microwave irradiation for 2 hours. At that time, the vial was cooled to room temperature and the reaction mixture was diluted with ethyl acetate and filtered through a pad of Celite with aid of ethyl acetate. The filtrate was washed with brine (3×), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes as elutant) to provide benzyl 3-(isopropylamino)benzoate (5).

Provenance & Evidence