Synthetic Route of 41965-95-1,Some common heterocyclic compound, 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, molecular formula is C8H11Cl2NO, 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.
N,N-Diisopropylethylamine (4.0 mL, 22.9 mmol, 4.0 eq.) was added to a mixture of 28 (2.0 g, 5.23 mmol, 1.0 eq.) and (3-chloro-4-methoxyphenyl)methanamine hydrochloride [29] (1.8 g, 8.41 mmol, 1.6 eq) in n-propanol (40 mL). The resulting mixture was heated at reflux for 16 h. After cooling to room temperature, water (40 mL) was added to the reaction mixture. The formed precipitate was filtered, washed successively with water (20 mL) and ethanol (20 mL) and then dried in a desiccator to afford the desired product 29 (2.3 g, 4.44 mmol, 85%) as a white solid. Rf (SiO2, cyclohexane/ethyl acetate, 7/3, v/v): 0.48; Mp: 140-142 C; IR (cm-1): 1701 (nuC=O), 1320 (nuCF3), 1281 (nuC-O), 1110 (nuC-O), 1031 (nuC-O); 1H NMR (CDCl3, 400 MHz) delta 9.79 (brs, 1H, NH), 9.33 (s, 1H, H2), 8.41 (m, 1H, H5), 8.18 (d, 1H, 4JH7-H5 = 1.5 Hz, H7), 7.40 (d, 1H, 4JH2?-H6?= 2.2 Hz, H2?), 7.24 (m, 1H, H6?), 6.96 (d, 1H, 3JH5?-H6?= 8.5 Hz, H5?), 4.87 (d, 2H, 3JHd-NH = 5.9 Hz, Hd), 4.40 (q, 2H, 3JHb-Hc= 7.1 Hz, Hb), 3.92 (s, 3H, He), 1.41 (t, 3H, 3JHc-Hb= 7.1 Hz, Hc); 13C NMR (CDCl3, 100 MHz) delta 167.3 (Ca), 154.5 (C4), 154.1 (2C, C4?, C8a), 148.6 (C2), 131.1 (C1?), 130.2 (C2?), 129.6 (C6?), 127.9 (C7), 126.2 (C8), 125.2 (q, 2JC6-F = 33 Hz, C6), 123.8 (d, 1JCF3-F = 271 Hz, CF3), 123.4 (C3?), 121.6 (C5), 120.1 (C4a), 113.4 (C5?), 105.9 (C3), 61.5 (Cb), 56.6 (Ce), 49.9 (Cd), 14.4 (Cc); HRMS calculated for C21H1779Br35ClF3N2O3 [M+H]+ m/z 517.0141, found C21H1779Br35ClF3N2O3 [M+H]+ m/z 517.0150 (77%); C21H1781Br35ClF3N2O3 or C21H1779Br37ClF3N2O3 [M+H]+ m/z 519.0163 (100%); C21H1781Br37ClF3N2O3 [M+H]+ m/z 521.0134 (24%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-4-methoxybenzylamine Hydrochloride, its application will become more common.
Reference:
Article; Liu, Jianrong; Maisonial-Besset, Aurelie; Wenzel, Barbara; Canitrot, Damien; Baufond, Ariane; Chezal, Jean-Michel; Brust, Peter; Moreau, Emmanuel; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 548 – 560;,
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