Imidazole → Guanethidine

関与物質

反応手順

First, 12 g (0.046 mol) of paradodecyl aniline was dissolved in 100 mL of THF and then put into a 100 mL three-neck round bottom flask. To the resulting mixture was added dropwise through a funnel for 10 minutes an acid remover prepared by mixing imidazole and triethyl amine at the same mole ratio (0.023 mol). Then, to the resulting mixture was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared by dissolving 3.8 ml (0.047 mol) of acryloyl chloride in 20 mL of THF. At this time, the reaction mixture cooled with ice in order for its temperature to be maintained below 5° C. Thereafter, the reaction proceeded at 0° C. for 6 hours, and at 25° C. for 9 hours. After the completion of the reaction, the resulting mixture was filtered with a filtering paper to remove salt precipitates, and then the solvent was eliminated by using an evaporator. The obtained solid was dissolved in 100 mL of dichloromethane and put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 and shaken strongly to separate the aqueous solution layer and remove an unreacted acryloyl chloride. To the dichloromethane solution as separated was added 1.0 g of magnesium sulfate and the resulting mixture was stirred for 5 hours and filtered so as to remove a trace amount of water being dissolved in the solvent. The resulting dichloromethane solution was evaporated and then 100 mL of n-hexane was added thereto and stirred for 2 hours, and then is filtered to remove an unreacted paradodecyl aniline remained in the solution. The solvent was removed from the resulting solution by using an evaporator to provide a white solid of DOPAM (Yield: 95%). The chemical structure of DOPAM as synthesized was confirmed by a 1H nuclear magnetic resonance (1H-NMR) spectrum, and the results are the same as follows:

情報源と証拠