The different functionalities of imine group found in many compounds are of important biological activity. Since, the development of novel imines is biologically encouraged, this study aims to develop a straightforward synthesis pathway of dihydroisoquinoline imines that could reveal antihypertensive effects. Starting from 2-méthyl-1-phényl-2-propanol, four different dihydroisoquinoline imines compounds (2a-d) were obtained and their structures were analyzed by mass spectrum, elemental analysis and NMR spectral studies. The crystal structure of 2b was determined from single crystal X-ray diffraction data.The newly synthesized compounds were evaluated for angiotensin I-converting enzyme (ACE) inhibition, using an enzymatic in vitro assay. The results were compared to Captopril as a reference drug. Compounds 2a, 2b and 2d showed inhibition activity with IC50 values of 0.15, 0.13 and 0.40 mg/ml, respectively. The docking of chemical compounds in the ACE active site explained the higher inhibitory capability of compounds 2a and 2b on the catalytic activity of the enzyme, indicating a potential anti-hypertensive effect of these compounds.