Benzene, 1-chloro-3-isocyanato- → N-(3-chlorophenyl)-4-(2-(trifluoromethyl)phenoxy)piperidine-1-carboxamide

A solution of 4-(2-trifluoromethylphenoxy)piperidine hydrochloride (42 mg, 0.15 mmol), 3-chlorophenyl isocyanate (36 mg, 0.30 mmol), and N,N-diisopropylethylamine (78 μL, 0.45 mmol) was stirred in dichloromethane (2 mL) at room temperature for overnight. The reaction mixture was diluted with dichloromethane and the solution was washed successively with 1N HCl, and NaHCO3 (sat.)/brine. The organic fraction was dried over MgSO4, filtered, and concentrated. The compound was purified by radial silica gel chromatography (1:20 to 1:2 ethyl acetate:hexanes) to afford the product which was 98% pure by LCMS analysis (15.7 mg, 26%).

1. washthe solution was washed successively with 1N HCl, and NaHCO3 (sat.)/brine
2. dry with materialThe organic fraction was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customThe compound was purified by radial silica gel chromatography (1:20 to 1:2 ethyl acetate:hexanes)
6. customto afford the product which

ORD record

ord-5945733f9abc4babaa5c79a78509b4b6

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915293B2