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Properties of substance:

lidocaine

Synonyms:

2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

Group of substances:

organic

Physical appearance:

needles crystals

Empirical formula (Hill's system for organic substances):

C14H22N2O

Structural formula as text:

(CH3)3C6H2NHCOCH2N(C2H5)2

Melting point (°C):

68-69

Solubility (g/100 g of solvent):

benzene: soluble [Ref.]
chloroform: soluble [Ref.]
diethyl ether: soluble [Ref.]
ethanol: soluble [Ref.]
water: insoluble [Ref.]

Synthesis 1:

Reference: Stachowiak W., Wysocki M., Niemczak M. “Bitter” Results: Toward Sustainable Synthesis of the Most Bitter Substances, Denatonium Saccharinate and Denatonium Benzoate, Starting from a Popular Anesthetic, Lidocaine / Journal of Chemical Education. - 2022. - Vol. 99, No. 4 pp. S4-S5 [doi: 10.1021/acs.jchemed.1c00995]


(CH3)2C6H3NHCOCH2N(C2H5)2 * HCl * H2O + NaOH → (CH3)2C6H3NHCOCH2N(C2H5)2 + NaCl + 2H2O

In 60 ml of ethanol 21 g (73 mmol) of lidocaine hydrochloride monohydrate was dissolved. Then, 4.1 g (73 mmol) of potassium hydroxide or equimolar amount (2.9 g) of sodium hydroxide were added. The reaction mixture was stirred for 10 minutes. Next, the precipitated inorganic salt was filtered off and the solvent was evaporated from the filtrate, leaving 16.7 g (98% yield) of white, waxy substance.

Alternative process was performed in water with the same amounts of lidocaine and potassium hydroxide. The reagents were dissolved in 60 ml of water and white solid started to precipitate. Then, the sediment was washed several times with small amounts of water and dried in vacuum at 40°C for 48 hours. Yield of the reaction was 14.5 g (85%).

References:

  1. The Merck Index 11th ed., Merck & Company, 1989. - pp. 863

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru