With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.122833-04-9,2-Methoxy-4-(4-methylpiperazin-1-yl)aniline,as a common compound, the synthetic route is as follows.
To a solution of Int-14 (100 mg, 0.335 mmol) and 2-methoxy-4-(4-methylpiperazin-l-yl)aniline (82 mg, 0.369 mmol) in 2- methoxyethanol (2 mL) was added 4 M HC1 in dioxane (0.086 mL, 0.343 mmol). The solution was stirred and heated at 110 C for 14 h. Then, additional 2-methoxy-4-(4-methylpiperazin-l- yl)aniline (40 mg, 0.180 mmol) and 1 drop of 4 M HC1 (aq) were added and the mixture was further irradiated under microwave conditions for 15 minutes at 160 C. Work up in the same way as Ex-20 provided the title compound as a light brown foam (97 mg, 60%). HPLC: 99% [tR = 8.7 min, 45% MeOH, 55% water (with 0.1% TFA), 20 min. NMR (400 MHz, DMSO-ifc): delta 7.83 (d, J = 8.8 Hz, 1H), 7.82 (s, 1H), 7.42 (s, 1H, disappeared on D20 shake), 7.18 (ddd, J = 8.2, 7.4, 1.7 Hz, 1H), 7.14 (t, / = 6.3 Hz, 1H, reduced by 50% on D20 shake), 7.07 (dd, / = 7.4, 1.7 Hz, 1H), 6.94 (dd, / = 8.2, 0.9 Hz, 1H), 6.85 (td, / = 7.4, 0.9 Hz, 1H), 6.60 (d, / = 2.5 Hz, 1H), 6.34 (dd, / = 8.8, 2.5 Hz, 1H), 3.79 (s, 3H), 3.76 (s, 3H), 3.50 (q, / = 6.3 Hz, 2H), 3.10- 3.03 (m, 4H), 2.82 (t, / = 6.3 Hz, 2H), 2.47-2.41 (m, 4H), 2.21 (s, 3H). HPLC-MS (ESI+): m/z 483.3 [50%, (M35C1+H)+], 242.2 [100%, (M35C1+2H)2+]. LC-MS (ESI+): 483.2 [100%, (M35C1+H)+]. HRMS (ESI+): m/z calcd for C25H31CI2N6O2 (M+H)+ 483.2270, found 483.2272., 122833-04-9
122833-04-9 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline 20136253, apiperazines compound, is more and more widely used in various fields.
Reference£º
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE; MAHAJAN, Nupam P.; MAHAJAN, Kiran N.; LAWRENCE, Nicholas J.; LAWRENCE, Hirshani R.; (85 pag.)WO2017/23899; (2017); A1;,
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