New downstream synthetic route of 2770-11-8

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Chlorophenoxy)aniline, and friends who are interested can also refer to it.

Reference of 2770-11-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2770-11-8 name is 2-(4-Chlorophenoxy)aniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

4-[2-(4-Chlorophenoxy)phenylcarbamoyI]piperidine-l-carboxylic acid fer/-butyl ester (AMR01031) C23H27ClN2O4, MW 430,92A solution of piperidine-l,4-dicarboxylic acid mono-tert-butyl ester (AMRO 1030, 417 mg, 1.82 mmol) in dry DCM (8 mL) was stirred under nitrogen, and 4- dimethylaminopyridine (DMPA, 40 mg, 0.327 mmol), (l-(3-dimemylaminopropyl)-3- ethylcarbodiimide hydrochloride (EDC, 1.05 g, 5.46 mmol) and triethylamine (0.25 mL) were added. The resulting mixture was stirred for 30 min under nitrogen and 2-(4-chloro- phenoxy)-phenylamine (AMR01029, 400 mg, 1.82 mmol) in dry DCM (4 mL) was added. After stirring at room temperature for 24 h, the mixture was diluted with DCM, washed EPO with HCl IM (3 x 25 mL), water, saturated NaHCO3 (2 x 25 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated. Flash chromatography on silica gel of the crude product using hexane/EtOAc 8:2 as eluent gave starting material (104 mg). Further elution using hexane/EtOAc 7:3 gave 4-[2-(4-chlorophenoxy)- phenylcarbamoyl]piperidine-l-carboxylic acid tert-butyl ester (430 mg, 55%) as a white solid, mp 97-99 0C. Rf: 0.22 (hexane/EtOAc 7:3) LC/MS (APCI) tr = 3.83 min, m/z 431.23 (33), 429.21 (M’-H,100). 1H NMR (270 MHz, CDCl3) ¡ê 1.44 (9H5 s, 3CH3), 1.68 (2H, m, CH2), 1.83 (2H, m, CH2), 2.36 (IH, tt, J= 11.4, 3.7 Hz), 2.75 (4 H, br t, 2CH2), 4.11 (4H, m, 2CH2), 6.81 (IH, dd, J= 8.2, 1.5 Hz, ArH), 6.93 (2H, AA’BB’, ArH), 7.01 (IH, td, ArH), 7.12 (IH, td, ArH), 7.31 (2H, AA’BB’, ArH), 7.68 (IH, br s, NH) and 8.40 (IH, dd, J= 6.9, 1.5 Hz, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Chlorophenoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics