Dicyclohexylcarbodiimide → HCID 19742818, compound

Participants

Reaction Steps

A mixture of 4-amino-5-chloro-2-[(3-iodophenyl)methoxy]benzoic acid (3.23 g, 8 mmol) and 1-hydroxybenzotriazole hydrate (1.23 g, 8 mmol) in anhydrous N, N-dimethylformamide (6 mL) under nitrogen was stirred for 30 minutes, treated with 1,3-dicyclohexylcarbodiimide (1.71 g, 8.3 mmol) in anhydrous N,N-dimethylformamide (2 mL), and stirred for 2 hours. A solution of 3-aminoquinuclidine (1.52 g, 12 mmol) in anhydrous N,N-dimethylformamide (4 mL) was added, and the mixture was stirred for 18 hours, filtered, and the filtrate concentrated in vacuo. The residue was dissolved in 20% methanol/tetrahydrofuran and filtered through a short column of alumina (eluted with 20% methanol/tetrahydrofuran). The filtrate was concentrated in vacuo and the residue was triturated from acetonitrile and recrystallized (2 crops) from 95% ethanol to afford 1.25 g (31%) of colorless solid; mp 196°-197° C.

Provenance & Evidence