2-[4-(Aminomethyl)phenyl]benzonitrile → HCID 10457125, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 319 mg (1 mmole) of ethyl valerate 5-benzyl-5-methylsemioxamazone (from Step C), 312 mg (1.5 mmole) of [(2'-cyanobiphenyl-4-yl)methyl]amine (from Step D), and 3 ml of dry ethanol was stirred under N2 in an oil bath at 50° C. for 2 hours and then at 70° C. for an additional 22 hours. The solution was concentrated in vacuo, and a solution of the residue in 30 ml of ethyl acetate was washed with 2×25 ml of 2 N HCl followed by 25 ml of saturated NaHCO3. The dried (MgSO4) ethyl acetate phase was filtered and concentrated. Column chromatography of the residue on silica gel (gradient elution using 0.25-5% isopropanol in CH2Cl2 gave 353 mg (76%) of the title compound as a hard glass, mp >40° C. (gradual), homogeneous by TLC in 19:1 CH2Cl 2 --MeOH; mass spectrum (FAB) m/e 464 (M+i)+. NMR indicated approximately a 1:1 ratio of amide rotamers.

Provenance & Evidence