1581275-16-2Relevant articles and documents
Benzo[D]imidazole derivatives of piperidine and piperazine
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Page/Page column 13; 14; 17, (2014/12/09)
The benzo[d]imidazole derivatives of piperidine and piperazine are 5-piperazinyl and 5-piperadinyl-1H-benzo[d]imidazol-2(3H)-ones that exhibit D2 and 5-HT1A receptor binding affinities, making them suitable for use as the active ingredient of pharmaceuticals for the treatment of schizophrenia. The derivatives have the general formula: where X is carbon or nitrogen and R is a selected biaryl group, or a pharmaceutically acceptable salt thereof. The piperidinyl compounds are prepared by removal of the Boc group from tert-Butyl-4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate. Subsequent reductive amination with a selected biarylaldehyde completes the synthesis of the 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones. The piperazinyl compounds are prepared by preparation of the intermediate tert-Butyl 4-(3,4-diaminophenyl)piperazine-1-carboxylate. Removal of the Boc group and subsequent reductive amination with a selected biarylaldehyde completes the synthesis of the 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones.