GENERAL STEPS: Methyl 4-acetylbenzoate (1.07 g, 6 mmol), methylamine (33% ethanol solution, 4.5 mL), methylamine hydrochloride (1.62 g, 24.0 mmol), and sodium cyanoborohydride (0.56 g, 9.0 mmol) were dissolved in a solvent mixture of tetrahydrofuran (12 mL) and methanol (7 mL). The reaction mixture was stirred at 65 °C for 16 hours. Upon completion of the reaction, the reaction solution was concentrated in vacuum and the residue was redissolved in dichloromethane (20 mL) and washed with deionized water (20 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuum to give the crude methyl 4-(1-aminoethyl)benzoate, which could be used in the next reaction without further purification. Yield: 0.86 g, 75% yield. LCMS analysis (Method B): retention time 0.98 min, purity 89%; m/z 194.05 ([M+H]+, 100%).
