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

Participants

Reaction Steps

To a stirred suspension of NH4Cl (2 g, 37.29 mmol) in dry toluene (50 mL) was added tri-methyl aluminium (2M in toluene) (18.6 mL, 37.29 mmol) at 5° C. The reaction mixture was then warmed to room temperature and stirred for 2 h. A solution of (1-phenyl-cyclopentyl)-acetonitrile (280) (2.3 g, 12.4 mmol) in toluene (10 mL) was added to the reaction mixture and stirring continued at 80° C. for 14 h. After completion of the reaction, the reaction mixture was quenched with a suspension of silica gel (8 g) in chloroform (8 mL) at 0° C. The reaction mixture was further stirred for 30 min at room temperature and filtered through a short bed of celite, washed with methanol and the combined filtrates were concentrated. The residue was stirred with 10% methanol in dichloromethane (200 mL). The white solid was discarded by filtration and filtrate was concentrated to get 2-(1-phenyl-cyclopentyl)-acetamidine hydrochloride salt (281) 2.5 g, 99.4% (crude yield) as a yellow gummy oil.

Provenance & Evidence