Abstract: The target compound of ω-aminomethyl longifolene(5) was synthesized from ω-chloromethyl longifolene(3) by Gabriel synthesis via intermediate N-substituted phthalimide derivative(4). The structures of compounds 4 and 5 were confirmed by high resolution mass spectrum(HRMS), Fourier transform infrared(FT-IR), ¹H nuclear magnetic resonance(¹H NMR), ¹³C nuclear magnetic resonance(¹³C NMR) and single-crystal X-ray diffraction(SC-XRD). The absolute configuration of compound 5 was inferred from the crystal structure of the synthesized compound 4. In the hydrolysis reaction of compound 4, the yield of compound 5 could be improved and the separation and purification process could be simplified by adding sodium hydroxide and heating reflux hydrazinolysis conditions under solvent-free. The results of single-factor experiment showed that under the optimum hydrazine hydrolysis conditions of n(hydrazine hydrate): n(compound 4)=23:1, 5 g 10% sodium hydroxide solution, and 6 h reaction time at reaction temperature of 120 ℃, the yield and purity of compound 5 could be reached 94.1% and 99.98%, respectively. The results of antibacterial activity assay in vitro showed that compound 5 could significantly inhibit the growth of four bacteria(Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Klebsiella pneumoniae) and three fungi(Candida albicans, Candida tropicalis and Aspergillus niger). The minimum inhibitory concentrations(MIC) were 1.95, 1.95, 7.81, 3.91, 3.91, 1.95 and 15.63 mg/L, respectively. Among them, compound 5 showed stronger inhibitory activities against C. albicans and C. tropicalis than positive control ketoconazole.