Methanol → 2-(1-Naphthalen-1-yl-cyclopentyl)-acetamidine

Participants

Reaction Steps

To a stirred suspension of NH4Cl (2.659 g, 49.72 mmol) in dry toluene (80 mL) was added tri-methyl aluminum (2M in toluene, 25.0 mL, 49.72 mmol) slowly at 5° C. then warm to room temperature and stirred for 2 h. A solution of (1-naphthalen-1-yl-cyclopentyl)-acetonitrile (342) (3.9 g, 16.57 mmol) in toluene (5 mL) was added to the above reaction mixture and stirred for 18 h at 85° C. (reaction was monitored by LC-MS). The reaction mixture was cooled to 0° C. and quenched with a suspension of silica gel in chloroform and then stirred for 0.5 h at room temperature. After being filtered through a sintered funnel, the residue was washed well with methanol and the combined filtrate was concentrated under reduced pressure to get a crude mass. 10% methanol in dichloromethane was added to the residue, from which the insoluble material was again filtered off and the filtrate was concentrated in vacuum to get semi pure 2-(1-naphthalen-1-yl-cyclopentyl)-acetamidine; hydrochloride (343) (4.5 g) as a brown sticky mass. This raw product was used in the next step without purification.

Provenance & Evidence