Acetonitrile → HCID 178512317, compound

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.

1. customThe solvent was removed by reduced pressure
2. additionthe remaining white solid was diluted with CH2Cl2 and H2O
3. extractionextracted 3× with CH2Cl2
4. customthe solvent removed by reduced pressure
5. customyielding a crude white solid
6. temperatureThe reaction was heated
7. temperatureto reflux for 24 hr
8. temperatureThe reaction mixture was cooled
9. customthe solvent removed by reduced pressure
10. customThe crude product was triturated with ether
11. filtrationcollected by filtration

ORD record

ord-051a71cc113746bf8d8f30e5be582a79

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495004B2