Acetonitrile → HCID 178512317, compound

Participants

Reaction Steps

A solution of diphenylcyanocarboimidate (10 g, 42 mmol) in 168 mL CH2Cl2 was treated with 2-chloro-6-fluorobenzylamine (6.7 g, 42 mmol) and diisopropylethylamine (7.3 mL, 42 mmol). The reaction mixture was stirred at room temperature for 24 hr. The solvent was removed by reduced pressure and the remaining white solid was diluted with CH2Cl2 and H2O and extracted 3× with CH2Cl2. The organic layers were combined and the solvent removed by reduced pressure yielding a crude white solid. This intermediate (12.8 g, 42 mmol) was dissolved in 80 mL acetonitrile and treated with piperidine (6.2 mL, 63 mmol). The reaction was heated to reflux for 24 hr. The reaction mixture was cooled and the solvent removed by reduced pressure. The crude product was triturated with ether and collected by filtration to yield a white solid (10 g, 82% yield): 1H NMR (CDCl3, 400 MHz) 7.28-7.23 (m, 1H), 7.22-7.18 (m, 1H), 7.04-6.98 (m, 1H), 4.94-4.85 (m, 1H), 4.68-4.63 (m, 2H), 3.45-3.39 (m, 4H), 1.65-1.57 (m, 6H); MS (ESP+) m/e 295 (MH+); Analytical CHN.

Provenance & Evidence