N-(2-Cyanoethyl)-N-methylaniline

General procedure: In a typical experiment, a mixture of amine (11 mmol), methacrylate or acrylonitrile (2 mmol), and Ps-AlCl3 (0.53 g, 0.24 mmol AlCl3 for aromatic amines; 0.27 g, 0.12 mmol AlCl3 for aliphatic amines) was stirred at 70 C for aromatic amines, room temperature for aliphatic amines. After completion of the reaction, Ps-AlCl3 was filtered and washed with ethyl acetate (3 10 ml), dried, and used in the next run under the same reaction conditions. The filtrate was concentrated to give the crude product, which was purified further by column chromatography (petroleum ether/ethylacetate or methanol/ethyl acetate).An activated carbon supported platinum catalyst (Pt / C, 0.06 mg platinum, 0.0003 mmol, 0.1 molpercent) was added to a 10 mL Schlenk tube, After evacuation of argon, add 1 mL of solvent (toluene).Under argon protection, to the above system, Were successively added with phenylsilane (78.9 mg, 0.75 mmol), III-12 (R2 =Phenyl, R3 = 2-cyanoethyl) (43.9 mg, 0.3 mmol) and formic acid (27.6 mg, 0.6 mmol). The whole antiThe reaction was carried out at 80 ° C with stirring for 15 hours.After completion of the reaction, 3 mL of ethyl acetate was added to the system, The reaction was quenched with aqueous sodium hydroxide (3 mol / L, 3 mL)Ethyl acetate (3 x 10 mL), the organic phase was separated, Dried over anhydrous Na2SO4, filtered, The solvent was removed by rotary evaporation.The residue was purified by column chromatography on ethyl acetate / petroleum ether = 1: 50 mixed solvent, Separation and purification gave the title product IV-1226.4 mg, yield 55percent.1) Under the protection of nitrogen, In a glove box 0.5 mmol of 3- (anilino) propionitrile, 8 equiv PMHS (4 mmol Si-H), 2.5 molpercent potassium phosphate, 5 molpercent 18-crown-6, 3.2 ml acetonitrile were added to a 100 ml schlenk tube.2) The N2 in the schlenk tube is replaced with CO2 as the C1 source by means of a double-tube tube in a liquid nitrogen-cooled freeze-plow operation and the CO2 pressure is 1 bar.3) The reaction was carried out at 80 ° C for 24 hours.4) After the reaction was separated by column chromatography, The stationary phase was silica gel, the mobile phase was petroleum ether and ethyl acetate, and the volume ratio was 9: 1.Bruker nuclear magnetic resonance, the final target productN-methyl-N-cyanoethylaniline (shown in Figures 3 and 4), Isolated yield 93percent.

Molecular Weight:160.22
XLogP3:1.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:160.100048391
Monoisotopic Mass:160.100048391
Topological Polar Surface Area:27
Heavy Atom Count:12
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes