How is lidocaine synthesized?
Lidocaine, 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide (2.2. 2), is synthesized from 2,6-dimethylaniline upon reaction with chloroacetic acid chloride, which gives α-chloro-2,6-dimethylacetanilide (2.1. 1), and its subsequent reaction with diethylamine [11].
Why is toluene used in the synthesis of lidocaine?
Toluene is used as the solvent in the reaction because it displays a higher boiling point than most of the other solvents that are usually used in the lab. Its low polarity causes the ionic byproduct to precipitate.
What three roles does diethyl amine serve in this synthesis?
Diethyl amine serves three roles in this reaction: (a) as a nucleophile to displace chloride anion from –CH2Cl in the α-chloro-2, 6-dimethylacetanilide by an SN2 type reaction; (b) as a base to absorb the HCl that is formed in the nucleophilic substitution reaction leading to Lidocaine; and (c) as a solvent for the …
How do you recrystallize lidocaine?
Lidocaine is highly soluble in all common organic solvents but it can be recrystallized from warm hexane using 1 mL of solvent per gram of crude product.
Why is glacial acetic acid used in lidocaine synthesis?
b. Glacial acetic acid is used as solvent in the reaction to dissolve 2,6-dimethylnitrobenzene, which does not dissolve in the strongly ionic aqueous solution.
Why was diethyl amine used in excess in the preparation of lidocaine reaction?
Excess diethylamine is also able to drive the reaction forward due to Le Chatlier’s Principle, as more is added the reaction will want to use up the excess in order to achieve equilibrium, shifting the reaction to the right.
Who synthesized lidocaine?
Lidocaine was discovered from systematic investigations at the Institute of Chemistry at Stockholm University (Stockholms Högskola), Stockholm. In the early 1930s, Hans von Euler-Chelpin, Ph.
How do you extract alkaloids?
Alkaloids are extracted as their salts together with accompanying soluble impurities. 3. The acidic extract is shaken with chloroform or other suitable organic solvent to remove pigments and other undesirable impurities (weak bases may be present).
How do you extract chemicals from plants?
Extraction is the first step to separate the desired natural products from the raw materials. Extraction methods include solvent extraction, distillation method, pressing and sublimation according to the extraction principle. Solvent extraction is the most widely used method.
What is the mechanism of action of lidocaine?
Lidocaine can block Na+ and K+ ion channels and regulate intracellular and extracellular calcium concentrations through other ligand-gated ion channels. Lidocaine was the first sodium channel blocker to be identified. Its main mechanism of action is blocking voltage-gated Na+ channels (VGSC/NaVs).
The synthesis of Lidocaine may be envisioned as outlined in the retrosynthesis in figure 2 below. The indicated carbon-nitrogen bond (a wavy line through the bond) in Lidocaine can be formed via the Sn2 reaction between commercially available diethyl amine andsynthetic intermediate α-chloro amide .
How do you make a carbon nitrogen bond in lidocaine?
The indicated carbon-nitrogen bond (a wavy line through the bond) in Lidocaine can be formed via the Sn2 reaction between commercially available diethyl amine andsynthetic intermediate α-chloro amide . Intermediate 1 1 is obtained via the commercially available compounds 2-chloroacetyl chloride and 2,6-dimethylaniline.
How do you make the bisulfate salt of lidocaine?
D. Synthesis of the bisulfate salt of lidocaine Dissolve the lidocaine in ether (10 mL per gram of lidocaine) and add 2 mL of 2.2 sulfuric acid in ethanol per gram of lidocaine. Stir and scratch with a glass rod to mix and induce crystallization.
Is lidocaine the same as hydrochloride?
(The hydrochloride is the salt generally used in medicine, but it is considerably more difficult to purify.) Lidocaine (the generic name) is sold under various trade names, the most common of which is Xylocaine.