Phenethylamine → HCID 21217929, compound

Participants

Reaction Steps

Part A. 4-(cyano)-beta-[3-(cyano)phenyl]benzene pentanoic acid (0.150 gm, 0.49 mmol) was dissolved in dry DMF and phenethyl amine (0.065 gm, 0.54 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.140 gm, 0.74 mmol) and 4-dimethylaminopyridine (0.150 gm, 1.2 mmol) were added. The resulting solution was stirred at room temperature for 48 hrs., quenched in 1 N HCl and extracted with ethyl acetate. The organic phase was washed with 1 N HCl, water and brine and dried over MgSO4. After removal of the solvent, the residue was chromatographed on silica gel eluting ethyl acetate:toluene(30:70, v:v) to give 4-(cyano)-beta-[3-(cyano)phenyl]-N-(2-phenylethyl)benzenepentanamide as an oil 0.100 gm (50%). MS: (M+H)+ 408; 1H NMR (CDCl3): 1.9 (m,1H), 2.35 (dd, 1H), 2.45 (m, 2H), 2.7(m, 3H), 3.25(m, 1H), 3.45 (m, 3H), 7.0 (d, 2H), 7.2 (m, 6H), 7.45 (m, 3H), 7.55 (m, 3H).

Provenance & Evidence