Diisopropylethylamine → HCID 86641647, compound

Participants

Reaction Steps

To a stirred solution of (1-benzyl-piperidin-4-yl)-(4-trifluoromethyl-thiazol-2-yl)-amine (D8) (0.57 g, 1.68 mmol) and diisopropylethylamine (1.04 ml, 5.88 mmol) in dichloromethane (15 ml) at 0° C., was added 1-chloroethyl chloroformate (0.45 ml, 4.2 mmol). The reaction mixture was stirred at room temperature for 3 h. and after this period, diluted with dichloromethane and extracted with a saturated solution of sodium hydrogen carbonate (5 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was dissolved in methanol (5 ml) and the reaction mixture was stirred at reflux for 3 h. After evaporation of the solvent, the crude product was purified by column chromatography (silica gel; 5-8% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. The crude product was crystallized from acetonitrile to yield D9 (0.34 g, 81%) as a white solid. C9H12F3N3S requires 251. Found 252 (MH+).

Provenance & Evidence