反应详情

温度

120 °C

Magnesium methyl carbonate (1.2 moles, 2 N in dimethylformamide) is heated to 120°C. under an atmosphere of carbon dioxide. The compound 5-methyl-6-phenyl-3,5-hexadien-2-one, 53.0 g (0.285 mole) is added and the mixture is stirred at 120°C. for a period of 4 hours under a stream of nitrogen while permitting the methanol that forms to escape. The mixture is allowed to cool under an atmosphere of carbon dioxide and 57.0 g (0.68 mole) of 2,3,4,5-tetrahydropyridine (as α-tripiperidein) is added and stirred at room temperature under an atmosphere of carbon dioxide for a period of 70 hours. The reaction mixture is poured into a concentrated HCl-ice mixture and extracted with methylene dichloride. The extracts are combined, washed with water, dried over anhydrous sodium sulfate, and the solvent removed. The crude 5-methyl-6-phenyl-1-(2-piperidyl)-3,5-hexadein-2-one which remains is recrystallized twice from isopropyl alcohol as the hydrochloride salt and is obtained in 48% yield (41.6 g) and has a M.P. of 179-80°C.

1. temperatureto cool under an atmosphere of carbon dioxide
2. stirringstirred at room temperature under an atmosphere of carbon dioxide for a period of 70 hours
3. extractionextracted with methylene dichloride
4. washwashed with water
5. dry with materialdried over anhydrous sodium sulfate
6. customthe solvent removed
7. customThe crude 5-methyl-6-phenyl-1-(2-piperidyl)-3,5-hexadein-2-one which remains is recrystallized twice from isopropyl alcohol as the hydrochloride salt
8. customis obtained in 48% yield (41.6 g)