Methylation method for amine
A technology of methylation and methylaniline, applied in the field of methylation of amines, can solve the problems of high toxicity of methylation reagents and expensive catalysts, and achieve the effects of low cost, low toxicity and high yield
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Embodiment 1
[0016] Preparation of 4-fluoro-N,N-dimethylaniline:
[0017] 1) In the glove box, 0.25mmol 4-fluoro-N-methylaniline, 6equiv (1.5mmol) diphenylsilane, 10mol% (based on 4-fluoro-N-methylaniline) cesium carbonate, 1.6ml acetonitrile solvent Add to a 50ml N2 protected schlenk tube.
[0018] 2) Remove the N in the schlenk tube through a double row of tubes under freezing and vacuum operation. 2 replaced by CO 2 , CO 2 The pressure is 1 bar.
[0019] 3) Using the cesium carbonate as a catalyst, the carbon dioxide as a C1 source, and the diphenylsilane as a reducing agent, react the 4-fluoro-N-methylaniline in an acetonitrile solvent at 80°C 72 hours.
[0020] 4) After the reaction, add 0.2 mmol of ferrocene into the schlenk tube as the NMR internal standard.
[0021] 5) Through Bruker nuclear magnetic analysis, the nuclear magnetic spectrum of the obtained product is consistent with the literature (Z.Yang, B.Yu, H.Zhang, Y.Zhao, G.Ji, Z.Ma, X.Gao, Z.Liu, GreenChem. 2015, 17, ...
Embodiment 2
[0023] Preparation of N-methyl-N-benzylaniline:
[0024] 1) In the glove box, 0.25mmol N-benzylaniline, 6equiv (1.5mmol) diphenylsilane, 10mol% (based on N-benzylaniline) cesium carbonate, and 1.6ml acetonitrile solvent were added to 50mlN 2 Protect the tube under the schlenk.
[0025] 2) Remove the N in the schlenk tube through a double row of tubes under freezing and vacuum operation. 2 replaced by CO 2 , CO 2 The pressure is 1 bar.
[0026] 3) Using the cesium carbonate as a catalyst, the carbon dioxide as a C1 source, and the diphenylsilane as a reducing agent, react the 4-fluoro-N-methylaniline in an acetonitrile solvent at 80°C 72 hours.
[0027] 4) After the reaction, add 0.2 mmol of ferrocene into the schlenk tube as the NMR internal standard.
[0028] 5) Through Bruker nuclear magnetic analysis, the nuclear magnetic spectrum of the obtained product is the same as that reported in the literature (M.-C.Fu, R.Shang, W.-M.Cheng, Y.Fu, Angewandte Chemie International...
Embodiment 3
[0030] Preparation of N-methylamantadine:
[0031] 1) In the glove box, 0.25mmol amantadine, 6equiv (1.5mmol) diphenylsilane, 10mol% (based on amantadine) cesium carbonate, and 1.6ml acetonitrile solvent were added to 50mlN 2 Protect the tube under the schlenk.
[0032] 2) Remove the N in the schlenk tube through a double row of tubes under freezing and vacuum operation. 2 replaced by CO 2 , CO 2 The pressure is 1 bar.
[0033] 3) Using the cesium carbonate as a catalyst, the carbon dioxide as a C1 source, and the diphenylsilane as a reducing agent, react the amantadine in an acetonitrile solvent at 80° C. for 72 hours.
[0034] 4) After the reaction, add 0.2 mmol of ferrocene into the schlenk tube as the NMR internal standard.
[0035] 5) Through Bruker nuclear magnetic analysis, the nuclear magnetic spectrum of the obtained product and the corresponding pure material spectrum reported in the literature (P.Besenius, P.A.G.Cormack, R.F.Ludlow, S.Otto, D.C.Sherrington, Che...
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