反应详情

A mixture of 27.3 g (0.15 mole) of p-bromobenzonitrile, 38.7 g (0.45 mole) of piperazine and 42.0 g (0.30 mole) of solid potassium carbonate in a total volume of 60 ml of n-butanol was heated at reflux for 16 hr under a nitrogen atmosphere. The mixture was concentrated under reduced pressure and the slurry partitioned between 10% sodium hydroxide and chloroform. The chloroform layer was separated, dried over magnesium sulfate and concentrated under reduced pressure to give an oil. The oil was eluted through a 400 g silica gel column with a 10% methanol in methylene chloride mixture. The appropriate fractions were concentrated under reduced pressure to give a golden oil. Trituration of this oil with ethyl acetate gave a white powder. The collected white powder was stirred for 15 min in ethereal hydrogen chloride and recrystallized from methanol-water to give 1.5 g (4.5%)* of white solid, m.p. 160° C. with decomposition.

1. temperaturewas heated
2. temperatureat reflux for 16 hr under a nitrogen atmosphere
3. concentrationThe mixture was concentrated under reduced pressure
4. customthe slurry partitioned between 10% sodium hydroxide and chloroform
5. customThe chloroform layer was separated
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customto give an oil
9. washThe oil was eluted through a 400 g silica gel column with a 10% methanol in methylene chloride mixture
10. concentrationThe appropriate fractions were concentrated under reduced pressure
11. customto give a golden oil
12. customrecrystallized from methanol-water
13. customto give 1.5 g (4.5%)* of white solid, m.p. 160° C. with decomposition