Synthetic Route of 13078-79-0, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, This compound has unique chemical properties. The synthetic route is as follows.
Triethylamine (153 muL, 1.10 mmol) was added dropwise at 0 C to a stirred suspension of 2-(1H-indol-3-yl)-2-oxoacetyl chloride (5; 208 mg, 1.00 mmol) and 2-(3-chlorophenyl)ethylamine (139 muL, 1.00 mmol) in anhydrous tert-butyl methyl ether (20 mL). The reaction mixture was stirred at 0 C for 15 min and then for 1 h at room temperature, monitoring the reaction by TLC analysis. After completion of the reaction the mixture was washed with a saturated NaHCO3 aqueous solution and water (3 × 20 mL in each case). The organic layer was dried over anhydrous Na2SO4 and evaporated. Recrystallization of the crude product from ethanol 70% yielded colourless crystals (33%).Mp.: 184-186 C; IR (KBr): 3347 cm-1 and 3190 cm-1 (NH), 2938 cm-1 (CH aliph.), 1657 cm-1 (CO); 1H NMR (DMSO-d6, 400.1 MHz): delta (ppm) = 2.88 (t, 2H, J = 7.0 Hz, NHCH2CH2), 3.50 (dt, 2H, J = 6.4/6.8 Hz, NHCH2CH2), 7.21-7.34 (m, 6H, ar-H), 7.52-7.57 (m, 1H, ar-H), 8.21-8.27 (m, 1H, ar-H), 8.67 (s, 1H, ar-H), 8.81 (t, 1H, J = 5.8 Hz, NH), 12.24 (s, 1H, indole-NH); 13C NMR (DMSO-d6, 100.6 MHz): delta (ppm) = 34.2 (CH2), 39.2 (CH2); 112.5, 121.2, 122.5, 123.4, 126.1, 127.5, 128.5, 130.1, 138.4 (tert. C); 112.1, 132.9, 136.3, 141.9, 163.6, 182.1 (quat. C, one signal is missing due to peak overlap); C18H15ClN2O2 (326.78); calcd. C 66.16, H 4.63, N 8.57; found C 65.84, H 4.60, N 8.31; HPLC-purity: 99.3% at 254 nm and 98.9% at 280 nm, tN = 3.38 min, tM = 1.03 min (ACN/H2O; 55:45), lambdamax: 256 nm and 327 nm.
The chemical industry reduces the impact on the environment during synthesis 2-(3-Chlorophenyl)ethanamine. I believe this compound will play a more active role in future production and life.
Reference:
Article; Schmidt, Stefanie; Preu, Lutz; Lemcke, Thomas; Totzke, Frank; Schaechtele, Christoph; Kubbutat, Michael H.G.; Kunick, Conrad; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2759 – 2769;,
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