Cyclohexanone → HCID 19770286, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of cyclohexanone (1.0 g, 10.0 mmole) in methylene chloride (10 ml) at -20° C., a 1M solution of titanium (IV) chloride in methylene chloride (20 ml) was added. The reaction mixture became yellow in color and to it a mixture of triethylamine (2.0 g, 20 mmole) and 2-amino-6-fluorobenzonitrile (1.36 g, 10.0 mmole) in methylene chloride (30 ml) were added. The reaction mixture immediately became dark in color and was allowed to warm to room temperature (about 25° C.) and stirred further for 15 hours. At the end of this period, the reaction mixture was treated with 12% aqueous NaOH (100 ml), and methylene chloride (100 ml). The reaction mixture was then filtered through a 2 inch diatomaceous earth pad (Celite (trademark)) which was washed with methylene chloride (50 ml) and water (100 ml). The organic layer was separated, washed with water (1×30 ml) and dried (anhydrous MgSO 4). The methylene chloride was removed under vacuum to afford an oil which was triturated with ether to give the title compound as a white solid (218 mg, 10%, m.p. 175° C.). 1H-NMR (CDCl3, 300 MHz,δ): 4H, m, 2.0 ppm; 2H, t, 2.59 ppm (J=7.0 Hz); 2H, t, 3.06 ppm (J=7.0 Hz); 2H, bs, 5.37 ppm; 1H, dd, 7.0 ppm (J=7.5, 14 Hz); 1H, dd, 7.46 ppm (J=8, 16 Hz); 1H d, 7.72 ppm (J=8.5 Hz). HRMS: Calculated--216.1053; Found--216.1039.

Provenance & Evidence