With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1121-22-8,trans-Cyclohexane-1,2-diamine,as a common compound, the synthetic route is as follows.
Into a solution containing 1,12-diisocyanatododecane (5.04 grams, 20 mmol; obtained from Sigma-Aldrich Fine Chemicals) and a 1:1 mixture of hexane and tetrahydrofuran (75 milliliters) stirring at room temperature was added a solution containing triethylene glycol monomethacrylate (4.36 grams, 20 mmol; obtained as CD570 from Sartomer Company Inc., Exton, Pa.) dissolved in a 1:1 mixture of hexane and tetrahydrofuran (25 milliliters), and dibutyltin dilaurate (0.063 grams, 0.1 mmol; obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of 40 C. The progress of the reaction was monitored by 1H-NMR spectroscopy for consumption of the triethylene glycol monomethacrylate reactant. The mixture was cooled to about 15 C. temperature, after which to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (1.14 grams, 10 mmol; obtained as a racemic mixture of (1R,2R) and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in a 1:1 mixture of hexane and tetrahydrofuran (20 milliliters). The reaction mixture was stirred for 1 hour while warming up to room temperature. FTIR spectroscopic analysis of a reaction sample showed little unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). Any residual isocyanate reagent was quenched by addition of methanol (5 milliliters), The reaction mixture was then filtered by vacuum filtration to give 10.11 grams of a solid product as a white powder (96 percent yield). The product was believed to be of the formulae 1H-NMR spectroscopic analysis of the solid was performed in DMSO-d6 (300 MHz) at room temperature (25 C.) and indicated the above structure with the following assigned peaks: 1.10-1.80 ppm (multiplet, 24 H integration, 20 protons from -NH-CH2(CH2)10CH2-NH- portion and 4 methylene protons from the cyclohexane ring portion); 1.90 ppm (singlet, 3 H integration, -(CO)C(CH3)CH2); 2.95 ppm (narrow multiplet, 4 H integration, -NH-CH2(CH2)10CH2-NH-); 3.35 ppm (multiplet, 1 H, cyclohexane ring methine proton); 3.55 ppm (narrow multiplet, 8 H integration, -(CH2-O) protons); 4.07 ppm and 4.27 ppm (broad singlets, each 2 H integration, NH(CO)OCH2CH2O- and -OCH2CH2O(CO)-C(CH3)CH2); 5.70 ppm and 5.88 ppm (broad singlet, each 1 H integration, urea NH protons); 5.70 ppm and 6.18 ppm (sharp singlet, each 1 H integration, terminal vinyl protons -(CO)C(CH3)CH2); 7.15 ppm (broad singlet, 1 H integration, urethane NH proton). Elemental analysis calculated for: C: 57.80%, H: 8.80%, N: 8.99%. Found for: C: 61.39%, H: 9.28%, N: 7.96%.
1121-22-8, As the paragraph descriping shows that 1121-22-8 is playing an increasingly important role.
Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare