Ammonium Chloride → 2-(1-p-Tolyl-cyclopentyl)-acetamidine

温度

0 °C

To a stirred suspension of NH4Cl (1.3 g, 23.69 mmol) in dry toluene (30 mL) was added trimethylaluminium (2M solution in toluene) dropwise at 0° C., stirred at 0° C. for 15 min, then stirred at room temperature for 2 h. The solution of [1-(4-trifluoromethyl-phenyl)-cyclopentyl]-acetonitrile (241) (2 g, 7.89 mmol) in toluene (10 mL) was added dropwise at the room temperature and the reaction mixture was heated at 80° C. for 16 h, the reaction mixture was cooled to 0° C., and the reaction mixture was poured into the slurry of silica gel (4 g) in CHCl3 (4 mL), stirred vigorously for 30 min at 0° C., the solid was filtered off through celite and washed with methanol (5×100 mL). The filtrate was concentrated and the crude product was taken up in 10% methanol in dichloromethane (200 mL) and stirred for 30 min. The solid was discarded by filtration and the filtrate was concentrated. The crude product was suspended in ether and a solid was collected by filtration and dried to get 2-(1-p-tolyl-cyclopentyl)-acetamidine (hydrochloride salt) (242) (1.4 g, 65.59%) as a light yellow solid.

1. stirringstirred at room temperature for 2 h
2. temperaturethe reaction mixture was heated at 80° C. for 16 h
3. temperaturethe reaction mixture was cooled to 0° C.
4. stirringstirred vigorously for 30 min at 0° C.
5. filtrationthe solid was filtered off through celite
6. washwashed with methanol (5×100 mL)
7. concentrationThe filtrate was concentrated
8. stirringstirred for 30 min
9. filtrationThe solid was discarded by filtration
10. concentrationthe filtrate was concentrated
11. filtrationa solid was collected by filtration
12. customdried

ORDレコード

ord-5b8b53a6dfa04642b183c513f2ca4aa1

出典データセット

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09045486B2