Water → HCID 178419544, compound

Participants

Reaction Steps

tert-Butyl 4-((3,4-diaminophenoxy)methyl)piperidine-1-carboxylate (10.18 mmoles, 3.27 g, 1 equivalent) was dissolved in acetonitrile (40 ml) and water (20 ml) and cooled to 0-5° C. (ice-water). Cyanogen bromide (1.112 g, 10.5 mmoles) 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 give 3.53 g of tert-butyl 4-((2-amino-1H-benzo[d]imidazol-5-yloxy)methyl)piperidine-1-carboxylate hydrobromide (yield 100%) which was used directly in the step. 1H-NMR (400 MHz, DMSO-d6) δ 12.22 (br s, 2H), 8.30 (s, 2H), 7.21 (d, 1H), 6.90 (s, 1H), 6.79 (d, 1H), 3.96 (m, 2H), 3.82 (d, 2H), 2.73 (m, 2H), 1.91 (m, 1H), 1.74 (d, 2H), 1.39 (s, 9H), 1.26 (m, 2H), MS (EI): 347 (MH+).

Provenance & Evidence