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ChemicalBook CAS DataBase List Nicotine
54-11-5

Nicotine synthesis

8synthesis methods
The nicotine molecule consists of a pyrrolidine ring attached to a pyridine ring by a bondbetween carbon atoms in the two-ring systems. Nicotine was isolated in impure form fromtobacco in 1809 by Louis Nicholas-Vauquelin (1763–1829). Vauquelin called the substancenicotianine. In 1826, Wilhelm Posselt (1806–1877) and Karl Ludwig Reimann (1804–1872),medical students at Heidelberg University, isolated pure nicotine and published dissertationson its pharmacology in 1828. Louis Henri Melsens (1814–1886) determined nicotine’sempirical formula. Amé Pictet (1857–1937) and P. Crépieux reported the synthesis of nicotine in 1903.
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Yield:54-11-5 95%

Reaction Conditions:

with formic acid in ethanol;water at 20;Inert atmosphere;

Steps:

1.4; 2.4; 3.4; 5.4; 6.4

(4) At room temperature, in a nitrogen atmosphere,(S)-(-)-3-pyrrolidinylpyridine (14.8g, 0.1mol) was added to the reactor,50 mL of ethanol, 10 mL of water, 2 mL of formic acid, and paraformaldehyde (4.0 g, 0.13 mol) were added to heat the reaction, and the reaction process was monitored by HPLC. After the reaction was completed, the temperature was cooled to 10°C, and the pH of the system was adjusted to 11.0 with a liquid alkali solution. Extract three times with toluene. The toluene phases were combined and concentrated under reduced pressure to recover toluene. Then high vacuum and reduced pressure distillation, vacuum degree -0.098Mpa, to obtain 15.5 g of colorless oil (S)-(-)-nicotine, the yield is 95%, the HPLC purity is 99.2%, and the ee% value is 99%.

References:

CN113999084,2022,A Location in patent:Paragraph 0022; 0027; 0028; 0033; 0034; 0039; 0040; 0045

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