Ammonium Chloride → 2-(1-Phenyl-cyclopentyl)-acetamidine HCl salt

Participants

Reaction Steps

To a stirred suspension of NH4Cl (5.9 g, 111.97 mmol) in toluene (200 mL) was added trimethylaluminium (2 Min toluene) (56 mL, 111.96 mmol) at 5° C. The reaction mixture was allowed to warm up to room temperature and stirred for 2 h. A solution of [1-(4-chlorophenyl)-cyclopentyl]-acetonitrile (321) (8.2 g, 37.32 mmol) in toluene (20 mL) was added to the reaction mixture at room temperature and the reaction mixture was heated at 80° C. for 14 h. After completion of the reaction, the reaction mixture was quenched with a suspension of silica gel (32 g) in chloroform (32 mL) at 0° C. The quenched mixture was stirred for 30 min at room temperature and filtered through a pad of celite. The residue was washed with methanol (5×50 mL) and the combined filtrate was concentrated. The residue was stirred in 10% methanol in dichloromethane (150 mL) and the resulting white solid was discarded by filtration and the filtrate was concentrated to get 2-(1-phenyl-cyclopentyl)-acetamidine, hydrochloride (322) (7 g, 79%, crude) as a yellow gummy oil.

Provenance & Evidence