Ethyl Acetate → 2-[1-(2,5-Dichlorophenyl)-cyclopentyl]-acetamidine hydrochloride

To a suspension of NH4Cl (1.939 g, 35.573 mmol) in toluene (30 mL) was added dropwise a solution of AlMe3 (2M in toluene; 9.48 mL, 18.972 mmol) at 0° C. and the mixture was stirred for 2 h at room temperature prior to the addition of a solution of [1-(2,5-dichlorophenyl)-cyclopentyl]-acetonitrile (202) in toluene (20 mL). It was then heated to 80° C. for 16 h. Silica thin layer chromatography was performed (40% ethyl acetate in hexane, Rf=0.1). The cooled reaction mixture was poured into a slurry of normal silica gel (100-200 mesh; 8 g) in CHCl3 (60 mL), followed by vigorous stirring for 30 min. The mixture was filtered off and the cake was rinsed with methanol. The combined filtrate was evaporated and the crude residue was taken in 10% methanol in dichloromethane (100 mL). The mixture was stirred for 30 min. The suspended solid was removed by filtration and the filtrate was evaporated. The crude product was triturated in diethylether and the solid was collected by filtration, dried under vacuum to afford 2-[1-(2,5-dichlorophenyl)-cyclopentyl]-acetamidine hydrochloride (203) (2.0 g, 62.2%) as a white solid.

1. temperatureIt was then heated to 80° C. for 16 h
2. customThe cooled reaction mixture
3. stirringby vigorous stirring for 30 min
4. filtrationThe mixture was filtered off
5. washthe cake was rinsed with methanol
6. customThe combined filtrate was evaporated
7. stirringThe mixture was stirred for 30 min
8. customThe suspended solid was removed by filtration
9. customthe filtrate was evaporated
10. customThe crude product was triturated in diethylether
11. filtrationthe solid was collected by filtration
12. customdried under vacuum

ORD 기록

ord-1224def955ad47e1a4a6ad7d17c4679c

출처 데이터셋

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09045486B2