Abstract: OBJECTIVE To study the synthetic process of evogliptin hydrochloride (1). METHODS Rac-evogliptin was synthesized from 2,4,5-trifluoro phenyl acetic acid through condensation, amination, and NaBH₄ reduction in three steps. After resolution of rac-evogliptin with L-(+)-tartaric acid and susequent salification process, the corresponding desired evogliptin hydrochloride was produced. In addition, another (S)-enantiomer could be recycled substantially as enamine intermediate via N-chlorination and elimination in two steps. RESULTS The yield of evogliptin hydrochloride was 26.9%. The purity of the target product was 99.9% with excellent enantioselectivity (99.8% ee). The recovery rate of enamine intermediate was 92.3% based on the resolution yield of the remaining enantiomers. CONCLUSION This synthetic process is a satisfactory way with high yield, simple synthetic route, low-cost, convenient operation for industrial production. Moreover, this mothod also provides an efficient and attractive strategy for the preparation of chiral amine drugs.