Sulfur → 1-(4-fluorophenylmethyl)-N-[1-{2-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]ethyl}-4-piperidinyl]-1H-benzimidazol-2-amine

Participants

Reaction Steps

A mixture of 6 parts of N-{2-[(4-fluorophenylmethyl)amino]phenyl}-N'-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]thiourea, 3.2 parts of mercury (II) oxide, 0.1 parts of sulfur. and 90 parts of tetrahydrofuran is stirred and refluxed for 3 hours. The reaction mixture is filtered over Hyflo and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of 2-propanone and 2,2'-oxybispropane, yielding 1.2 parts (20%) of 1-(4-fluorophenylmethyl)-N-[1-{2-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]ethyl}-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 196.9° C.

Provenance & Evidence