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 Production Method of N-Ethylpiperidine
  • Production Method of N-Ethylpiperidine
  • N-Ethyl (CAS NO.: ), which is also known as Piperidine, 1-ethyl-, could be produced through the following synthesis route.

    A 1-l. three-necked flask equipped with a reflux condenser, an inlet for dry nitrogen, and a mechanical stirrer is flushed with dry nitrogen. It is then charged with 340 g. (4.00 moles) of piperidine 4.4 g. (0.19 g. atom) of sodium, and 5.0 g. (5.1 ml., 0.063 mole) of pyridine. While a slow stream of nitrogen continues to pass through the flask, the solution is heated under reflux with high-speed stirring for approximately 10 minutes. During this time most of the sodium reacts without evolution of hydrogen, and the dispersion darkens. The dispersion, which contains some finely divided solids, is cooled and transferred to a 2-l. stirred autoclave under nitrogen. An additional 85 g. (1.00 mole) of piperidine is used to wash the last portions of the dispersion into the autoclave.

    The autoclave is pressured with ethylene to 400 lb./in.2 with stirring. It is then heated to 100° with stirring, which causes the pressure to rise to about 555 lb./in.2. It is maintained at 100° with stirring until a gradual drop in pressure ceases; this usually takes about 2.5 hours, but it may take as long as 10 hours. The autoclave is cooled to room temperature, and the excess ethylene is vented. The reaction mixture is transferred to a 1-l. round-bottomed flask, the autoclave is rinsed with 100 ml. of methanol that is added to the flask, and the mixture is fractionated through a 90-cm. column packed with glass helices. After a fore-cut of 50–100 g. distilling at 55–129°, 434–468 g. (77–83%) of N-ethylpiperidine is collected; b.p. 129–130.5°; nD20 1.443–1.444.


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