A new process to synthesize methyl (S/R)-4-(1-aminoethyl)benzoate from (S/R)-1-phenylethan-1-amine was studied. The starting material (S/R)-1-phenylethan-1-amine was trifluoroacetylated and then subsequent para-bromo substitution on phenyl ring gave (S/R)-N-(1-(4-bromophenyl)ethyl)-2,2,2-trifluoroethane (III). Next, lithium–halogen exchange of compound III with n-BuLi followed by the addition of CO2 and hydrolization afforded (S/R)-4-(1-(2,2,2-trifluoroacetamido)ethyl) benzoic acid (IV). The methyl (S/R)-4-(1-aminoethyl)benzoate hydrochloride (V) was accomplished after the amine deprotection and methyl esterification using thionyl chloride and methanol in a one-pot manner. This process has been successfully scaled up at a 2.5 kg scale in a molar yield of ~38%.