4-Methoxypiperidine → (4-Methoxy-piperidin-1-yl)-{(R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidin-3-yl}-methanone

Temperature

35 °C

Method M—Step a To a mixture of (R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride (obtained as described in general method 1, step d) (0.01 g, 0.30 mmol) (obtained as described in method A, step d) in dcm (2.5 mL), HATU (0.12 g, 0.33 mmol), TEA (0.09 mL, 0.63 mmol) and 4-methoxypiperidine (0.04 g, 0.33 mmol) were added. The reaction mixture was heated at 35° C. overnight, cooled to room temperature, washed with ammonium chloride solution (3 mL), filtered through a phase separator and organic solvent was removed. The crude was then purified by SCX column (eluent: first dcm:MeOH/1:1 then NH3 in MeOH (2N)) and flash chromatography (eluent: gradient from EtOAc:cyclohexane/10:0 to 0:10) to obtain 0.05 g of the title compound (38%).

1. additionwere added
2. temperaturecooled to room temperature
3. washwashed with ammonium chloride solution (3 mL)
4. filtrationfiltered through a phase separator and organic solvent
5. customwas removed
6. customThe crude was then purified by SCX column (eluent

ORD record

ord-d56fe85f2ba64ac698b8eb550fb3a895

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08835648B2