Triethylamine → HCID 86598934, compound

A solution of ethyl 2-methyl-2-[4-(2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (12 g; 29.34 mmol) and triethylamine (4.5 ml; 32.27 mmol) in 100 ml of dichloromethane was treated under nitrogen with cyanogen bromide (10.3 ml of a 3M solution in dichloromethane; 30.9 mmol). After 1.5 hr, additional triethylamine (2 ml) and cyanogen bromide (2.5 ml) were added and stirred another 30 minutes. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water (three times) and brine, dried over sodium sulfate and concentrated. Purification by flash chromatography using ethyl acetate-hexane mixtures (5–40% gradient) afforded ethyl 2-[4-(2-{cyano[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (10.9 g; 85% yield).