2,6-Dimethylbenzaldehyde → 1-[1-[1-(2,6-Dimethylbenzyl)piperidin-4-yl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

Participants

Reaction Steps

To a solution of 19.8 mg of 1-[1-(piperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one and 7.5 microliter of 2,6-dimethylbenzaldehyde in 1 ml of MeOH was added 274 microliter of 0.3M MeOH solution of ZnCl2—NaBH3CN at room temperature. The reaction mixture was stirred at room temperature for 2 h and quenched with saturated aqueous NaHCO3. The mixture was extracted with EtOAc, and the organic layer was washed with the 1:1 solution of saturated aqueous NaHCO3 and brine, and dried over anhydrous Na2SO4. The organic solvent was evaporated and the residue was purified with PNLC (CHCl3/MeOH/28% aqueous NH3=100/10/1) gave 11.8 mg of the target compound as a colorless solid.

Provenance & Evidence