Cinacalcet hydrochloride (11 g, 0.028 mol) in toluene (150 mL) was added to potassium carbonate (7.74 g, 0.056 mol) followed by 1-(3-bromopropyl)-3-(trifluoromethyl)benzene (14.95 g, 0.056 mol) under stirring at 25-30 °C. The reaction was heated and stirred at 110-111 °C for 48 h. Upon completion of the reaction (by TLC), the reaction was cooled and quenched with water (100 mL). The organic layer was separated, washed with water (100 mL), and concentrated under reduced pressure to obtain a thick oil. The crude oil was then purified by column chromatography on silica gel by eluting with chloroform to afford Cinacalcet Impurity D as a thick transparent oil.
