The general procedure for the synthesis of 1-(4-(2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-2-ol from 3-(1-naphthyloxy)-1,2-epoxypropane and 1-(2-methoxyphenyl)piperazine was as follows: with reference to the synthesis of Example 1 (RS)-naphthalenophenedil (HUHS1001), to a solution of 2-((1-naphthyloxy)methyl) ethylene oxide (100 mg, 0.50 mmol) to a solution of 2-(2-methoxyphenyl)piperazine (95 μL, 0.60 mmol) in ethanol (1 mL). The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford (RS)-naphthodil (199 mg, 100% yield). The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3) and ESI-HRMS (cation, sodium formate).1H-NMR data were as follows: δ 2.72-2.76 (m, 4H), 2.92-2.95 (m, 2H), 3.09-3.18 (m, 4H), 3.87 (s, 3H), 4.16 (dd, J = 9.6 and 5.0 Hz, 1H), 4.24 (dd, J = 9.6 and 5.0 Hz, 1H), 4.28-4.34 (m, 1H), 6.84 (d, J = 7.8 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H), 6.91-6.98 (m, 2H), 7.00-7.04 (m, 1H), 7.39 (t , J = 8.2 Hz, 1H), 7.44 (d, J = 8.2 Hz, 1H), 7.47-7.51 (m, 2H), 7.79-7.81 (m, 1H), 8.26-8.29 (m, 1H).ESI-HRMS (cation, sodium formate) Calculated value: C24H29N2O3 ([M + H]+) m/z 393.2173 , measured value 393.2148.
![2-[(1-Naphthyloxy)methyl]oxirane](/CAS/GIF/2461-42-9.gif)
