Ethoxyacetic acid → HCID 68670853, compound

Participants

Reaction Conditions

Reaction Steps

Method N—Step e To a solution of ethoxyacetic acid (0.05 mL, 0.49 mmol) in acetonitrile (3 mL) was added CDI as a stock solution (0.80 g, 0.49 mmol) and the resulting suspension was stirred at room temperature for 3 h. {1-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidin-4-ylamine hydrochloride (0.13 g, 0.41 mmol) and DIPEA (0.07 mL, 0.41 mmol) were added and the resulting solution heated at 70° C. overnight. The reaction was then cooled to room temperature, the solvent removed under reduced pressure. The crude product was redissolved in dichloromethane (4 mL) and washed with saturated Na2CO3 solution (2 mL) and water (2 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent: dichloromethane:MeOH, gradient from 100% dichloromethane to 95% dichloromethane:5% MeOH) to afford 0.70 g (44%) of the title compound.

Provenance & Evidence