Reaktion #164288

Reaktionsgleichung

(R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride

HATU

4-(N,N-dimethylamino)piperidine

→

NH3

title compound

Ausbeute 74.8%

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

Ausbeute 74.8%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturcooled to room temperature
3. 3
   Waschenwashed with ammonium chloride solution (3 mL)
4. 4
   Filtrationfiltered through a phase separator and organic solvent
5. 5
   Sonstigewas removed
6. 6
   SonstigeThe crude was then purified by SCX column (eluent

Vorschrift

Method N—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-(N,N-dimethylamino)piperidine (0.04 g, 0.35 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:NH3 in MeOH (2N)/10:0 to 9:1) to obtain 0.05 g of the title compound (37%).

Quelle