HCID 59707057, compound → HCID 59707066, compound

Participants

Reaction Steps

Palladium-on-charcoal (5%, 650 mg) was added to a solution of 1-(4-tert-butylbenzyl)-3-(4-nitrobenzyl)-1,3-dihydrobenzimidazol-2-one (P) (1.13 g, 2.73 mmol) in abs. MeOH (60 mL). The reaction mixture was subjected to a hydrogen pressure of 3 bar for 20 min at RT. The catalyst was separated by filtration, and the filtrate was concentrated in vacuo. The residue was taken up in EtOAc (10 mL) and filtered through a frit with kieselguhr (layer thickness 1 cm). The frit was washed with ethyl acetate (4×20 mL). The desired product 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-1,3-dihydrobenzimidazol-2-one (Q) was obtained in a yield of 960 mg (91% of theory). The corresponding hydrochloride was obtained by reaction of 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-1,3-dihydrobenzimidazol-2-one (Q) with chlorotrimethylsilane (1 mL, 7.9 mmol) in DCM (50 mL). The reaction mixture was stirred over a period of 17 h without exclusion of moisture, and the resulting solid matter was separated with the aid of a frit and then dried. The hydrochloride was obtained as solid matter (750 mg, 68% of theory, mp: 198-219° C.).

Provenance & Evidence