Synthetic Route of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Synthesis of 2-(((3- Methoxybenzyl)(methyl)amino)methyl)quinazolin-4(3H)-one (C). To a solution of 718 mg (3.69 mmol) of 2-(chloromethyl)-4(3H)-quinazolinone (A) in 6 mL of DMF was added 1.3 mL (1.34 g, 8.86 mmol) of 1-(3-methoxyphenyl)-N- methylmethanamine (B). The resulting solution was stirred at 120oC for 2 hours under microwave irradiation. After cooling to room temperature, the mixture was poured into 100 mL of water. The aqueous mixture stood for 5 minutes and then was extracted three times with 75-mL portions of ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude product was dissolved in minimal amount of ethyl acetate and precipitated by adding drops of hexanes to afford 629 mg (55%) of C as a light orange solid: 1H NMR (400 MHz, DMSO-d6) delta 11.95 (s, 1H), 8.12 (d, J = 8.0 Hz, 1H), 7.80 (td, J = 7.4, 1.2 Hz, 1H), 7.65 (d, J = 8.4 Hz, 1H), 7.50 (t, J = 7.6 Hz, 1H), 7.23 (t, J = 8.0 Hz, 1H), 7.01 (s, 1H), 6.95 (d, J = 7.6 Hz, 1H), 6.81 (dd, J = 8.0, 2.4 Hz, 1H), 3.75 (s, 3H), 3.61 (s, 2H), 3.56 (s, 2H), 2.19 (s, 3H); 13C NMR (100.5 MHz, DMSO-d6) delta 161.6, 159.2, 154.7, 148.4, 139.9, 134.3, 129.1, 127.0, 126.4, 125.8, 121.3, 121.1, 114.5, 112.5, 60.8, 59.8, 54.9, 41.5; ESI-HRMS m/z: [M+H]+ calcd for C18H19N3O2310.1550, found 310.1462.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(3-Methoxyphenyl)-N-methylmethanamine, its application will become more common.
Reference:
Patent; UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC.; CLARK, Geoffrey J.; TRENT, John O.; BURLISON, Joseph A.; (112 pag.)WO2017/19537; (2017); A1;,
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