Triethylamine → HCID 59164566, compound

Participants

Reaction Steps

To a solution of 5.20 g 3-(4-Cyano-3-methyl-phenyl)-propionic acid and 4.57 ml triethylamine in 100 ml tert-butanol 9.10 g diphenylphosphorylazide were given and the mixture heated under reflux overnight. The cooled reaction mixture was evaporated in vacuo. The resulting residue was dissolved in 150 ml ethyl acetate, washed with 50 ml citric acid/brine=1:1 and 50 ml saturated NaHCO3 solution and then dried over MgSO4. The residue was dissolved in 50 ml dichloromethane and 20 ml trifluoroacetic acid were added. The reaction mixture was stirred at room temperature for two hours. The solvent was removed in vacuo. The residue was coevaporated four times with portions of 100 ml toluene. The resulting brown residue was taken up in 50 ml acetonitrile and stirred at room temperature. The solid material was filtered off and dried in vacuo to obtain 2.45 g 4-(2-Amino-ethyl)-2-methyl-benzonitrile as its trifluoroacetate salt. The filtrate was evaporated in vacuo, the resulting residue was taken up in 100 ml diethyl ether and stirred at room temperature. The solid material was filtered off and dried in vacuo to obtain 1.17 g 4-(2-Amino-ethyl)-2-methyl-benzonitrile as its trifluoroacetate salt.

Provenance & Evidence