Dimethyl Sulfoxide → HCID 13769698, compound

Participants

Reaction Steps

To a stirred mixture of 5.1 parts of 4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidineethanol and 100 parts of dimethyl sulfoxide were added portionwise 0.9 parts of a sodium hydride dispersion 50%. After stirring for 1 hour at room temperature, 2.5 parts of 2-bromothiazole were added dropwise. Upon completion, stirring was continued overnight at room temperature. Water was added and the product was extracted twice with trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was taken up in 4-methyl-2-pentanone. The organic phase was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from methylbenzene, yielding 0.3 parts of 1-(2-furanylmethyl)-N-[1-[2-(2-thiazolyloxy)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 136.4° C. (compound 71).

Provenance & Evidence