According to the analysis of related databases, 2-(4-Chlorophenoxy)aniline, the application of this compound in the production field has become more and more popular.
2770-11-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2770-11-8 as follows.
Preparation of {4-[2-(4-chlorophenoxy)phenylamino]-piperidin-l-yl}- cyclohexylmethanone STX1702 C24H29ClN2O2, MW: 396.9785 EPO To a solution of 2-(4-chlorophenoxy)phenylamine (100 mg, 0.49 mmol), 1- cyclohexanecarbonyl-4-piperidone (154 mg, 0.735 mmol) and acetic acid (147 mg, 2.45 mmol) in DCE (1.5 ml) was added sodium triacetoxyborohydride (260 mg, 1.23 mmol). This solution was then heated at 1000C for 15 minutes in a CEM discover microwave (fixed hold time set to on). Further l-cyclohexanecarbonyl-4-piperidone (50 mg, 0.24 mmol) was added and this reaction mixture was again heated at 1000C for 10 minutes in the CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (5 ml) and extraction with ethyl acetate (3 x 5 ml) followed. The combined organics were dried (MgSO4), filtered and concentrated in vacuo and purification by flash chromatography proceeded (eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (58 mg, 30%). 1H NMR (270 MHz, CDCl3): delta 1.12-1.89 (12H, m, 12 x CH), 2.03-2.16 (2H5 m, 2 x CH)3 2.40-2.46 (IH, m, CH), 2.83 (2H, ‘t’, J= 11.1 Hz, CH2), 3.15 (IH, ‘t J= 12.4 Hz, CH), 3.49-3.54 (IH, m, CH), 3.83 (IH, bd, J= 13.9 Hz, CH), 4.0 (IH, s, CH)5 4.42 (IH, d, J= 14.1 Hz, NH)5 6.60-6.66 (IH, td5 J= 1.2, 1.5, 7.8 Hz, ArH)5 6.73-6.77 (IH5 dd5 J = 1.2, 8.2 Hz, ArH), 6.78-6.82 (IH, dd, J = 1.2, 7.9 Hz, ArH), 6.84-6.91 (2H, m, ArH)5 7.00- 7.06 (IH5 td, J = 1.5, 0.8, 7.5 Hz, ArH), 7.19-7.26 ppm (2H, m, ArH). 13C NMR (67.93 MHz, CDC13): delta 26.0, 29.4, 29.6, 32.2, 33.3, 40.5, 44.1, 49.9, 112.2, 117.2, 118.8, 119.6, 125.3, 127.9, 129.8, 138.9, 143.0, 156.1, 174.6 ppm LCMS: M+H: 413.47 HPLC: 100% (retention time 3.210 min, isocratic 90% acetonitrile : 10% water, 1 ml/min).
According to the analysis of related databases, 2-(4-Chlorophenoxy)aniline, the application of this compound in the production field has become more and more popular.
Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
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