As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,N1,N2-Dimethylethane-1,2-diamine,110-70-3,Molecular formula: C4H12N2,mainly used in chemical industry, its synthesis route is as follows.,110-70-3
The ligand 345BPMEN was synthesized by modifying thepreviously reported procedure (Singh et al. 2017). To a solutionof 2-chloromethyl-4-methoxy-3,5-dimethylpyridinehydrochloride 2.032 g (9.15 mmol) in 10 mL of water, asolution of potassium carbonate (2.55 g, (18.45 mmol) inwater (10 mL) was added dropwise. After potassium carbonateaddition, very thick white ppts were formed and solutionsolidified. Additional amount of water (50 mL) was addedinto the mixture. After water addition, the reaction mixturewas stirred at room temperature for next 30 min followed bysolvent extraction with dichloromethane (3 ¡Á 20 mL). Thecombined dichloromethane layer was treated with anhydroussodium sulfate. The solution was filtered, and the solventwas removed by rotatory evaporation. The collected light brown oil was dissolved in dichloromethane (10 mL).The above solution was added dropwise to a solution ofN,N?-dimethylethylenediamine 0.493 mL (4.58 mmol) indichloromethane (15 mL). Aqueous solution of 1 M sodiumhydroxide (10 mL) was slowly added and solution wasstirred for additional 60 h at room temperature. After 60 hof stirring was the rapid addition of a second fraction ofaqueous 1 M sodium hydroxide (10 mL, 10 mmol), the productwas extracted with dichloromethane (3 ¡Á 25 mL). Thecombined organic layers were dried over anhydrous sodiumsulfate and filtered. Subsequently, the excess solvent wasevaporated by vacuum to afford brown color viscous oil(1.71 g, Yield 97%). 1H NMR (500 MHz, Methanol-d4) delta8.08 (s, 2H, pyridine ring), 3.76 (s, 6H, -O-CH3-Py), 3.57(s, 4H, -CH2-CH2-Py), 2.56 (s, 4H, -CH2-CH2-), 2.28 (d,6H, CH3-Py), 2.24 (d, 6H, CH3-Py), 2.16 (s, 6H, -N-CH3).ESI-MS+: [345BPMEN + H]+ = 387.32 m/z+ (experimental)387.27 m/z+ (theoretical).
With the synthetic route has been constantly updated, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine,belong chiral-nitrogen-ligands compound
Reference£º
Article; Botcha, Niharika Krishna; Gutha, Rithvik R.; Sadeghi, Seyed M.; Mukherjee, Anusree; Photosynthesis Research; vol. 143; 2; (2020); p. 143 – 153;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis