反应详情

温度

0 °C

To a mixture of 0.03 mol of 3-(3-pyrrolidinomethylphenoxy)propylamine and 0.095 mol of pyridine in 100 ml of methylene chloride, stirred at 0° C., 0.047 mol of nicotinic acid 1-oxide chloride hydrochloride is added portionwise, then the resulting mixture is stirred 1 hour at room temperature and the solvent is evaporated off under reduced pressure. The residue is taken up with N hydrochloric acid and the salts obtained are eliminated by filtration, then the solution is extracted 3 times with 100 ml of ethyl acetate and sodium hydroxide is added thereto up to a basic pH. The solution is extracted 4 times with 100 ml of ethyl acetate, the organic phase is dried over anhydrous sodium sulfate and the solvent is evaporated off under reduced pressure. The oil thus obtained is chromatographied on silica, and eluted with methanol, the fractions of the pure product are collected and the solution thus obtained is treated with a solution of oxalic acid in ethanol; the precipitate which forms is crystallized from ethanol to yield 3.5 g of N-[3-(3-pyrrolidinomethylphenoxy)propyl]3-pyridinecarboxamide 1-oxide sesquioxalate CM 57891A; m.p. 115°-116° C. Yield: 30% of the theoretical value.

1. stirringthe resulting mixture is stirred 1 hour at room temperature
2. customthe solvent is evaporated off under reduced pressure
3. customthe salts obtained
4. filtrationare eliminated by filtration
5. extractionthe solution is extracted 3 times with 100 ml of ethyl acetate and sodium hydroxide
6. additionis added
7. extractionThe solution is extracted 4 times with 100 ml of ethyl acetate
8. dry with materialthe organic phase is dried over anhydrous sodium sulfate
9. customthe solvent is evaporated off under reduced pressure
10. customThe oil thus obtained
11. washeluted with methanol
12. customthe fractions of the pure product are collected
13. customthe solution thus obtained
14. customthe precipitate which forms is crystallized from ethanol