2-Chloroquinoline → 1-[(4-fluorophenyl)methyl]-N-[1-[2-(2-quinolinyloxy)ethyl]-4-piperidinyl]1H-benzimidazol-2-amine

Participants

Reaction Steps

5.5 Parts of 4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidineethanol and 135 parts of N,N-dimethyl-formamide were stirred at room temperature and 0.75 parts of a sodium hydride dispersion 50% were added. After stirring for one hour at room temperature, 2.5 parts of 2-chloroquinoline were added and the whole was stirred overnight at room temperature. The reaction mixture was poured onto water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile, yielding 4.3 parts (58%) of 1-[(4-fluorophenyl)-methyl]-N-[1-[2-(2-quinolinyloxy)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 149.9° C. (compound 77)

Provenance & Evidence