Water → HCID 178419545, compound

Participants

Reaction Steps

tert-Butyl 4-(3,4-diaminophenoxy)piperidine-1-carboxylate (5.673 mmoles, 1.914 g, 1 equivalent) was dissolved in acetonitrile (20 ml) and water (20 ml) and cooled to 0-5° C. (ice-water). Cyanogen bromide (5.67 mmoles, 0.721 g, 1.4 equivalents) was added in one lot and the reaction mixture was allowed to go to room temperature and stirred for 16 hours. The reaction mixture was then evaporated under reduced pressure to 2.41 g of tert-butyl 4-(2-amino-1H-benzo[d]imidazol-5-yloxy)piperidine-1-carboxylate hydrobromide (yield: 100%) which was used directly in the next reaction without any further purification. 1H-NMR (400 MHz, DMSO-d6) δ 12.22 (br s, 2H), 8.39 (s, 2H), 7.22 (d, 1H), 6.91 (s, 1H), 7.83 (d, 1H), 4.50 (m, 1H), 3.61 (m, 2H), 2.19 (, 2H), 1.90 (m, 2H), 1.40 (s, 9H). MS (EI): 333 (MH+).

Provenance & Evidence