Description

Medetomidine HCl exists in the form of white or almost white crystalline powder. It usually appears as a colorless or nearly colorless crystalline solid. Has good solubility in water. At room temperature, approximately 10 grams of water can be dissolved per gram. In addition, it can also be dissolved in organic solvents such as ethanol and methanol. Nuclear magnetic resonance (NMR) spectra, infrared spectroscopy (IR), and ultraviolet visible absorption spectroscopy (UV Vis) can be used for identification and quantitative analysis. Peracid base reaction, Redox and Substitution reaction can participate in a variety of chemical reactions to produce different derivatives or carry out structural modification. Its molecular structure contains benzene ring and imidazole ring, and contains an amino group and a substituted isopropyl group. Relatively stable under dry, dark, and sealed conditions.However, it is sensitive to light and is prone to degradation under sunlight or ultraviolet radiation. Therefore, attention should be paid to avoiding light during the preparation and storage process. It is a commonly used drug in clinical practice, belonging to α Adrenergic receptor agonists. It has the functions of sedation, analgesia and muscle relaxation, and is widely used in Veterinary medicine and human medicine.

We can provide 1- (2,3-dimethylphenyl) ethyl chloride, CAS 60907-88-2, hplc>95% (the analysis result more than 97%) ; (1-bromocyclopentyl)-2-thienyl ketone and n-(trimethyl) imidazole, CAS 18156-74-6 (purity>98%). Medetomidine HCl is a α2-adrenohormone protein kinase inhibitor. Its organic chemical name is (R)-4-(S)-[1-(2,3-dimethylphenyl) ethyl]-1H-imidazolium hydrochloride.

Chemical Formula

C13H16N2

Exact Mass

200.13

Molecular Weight

200.29

m/z

200.13 (100.0%), 201.13 (14.1%)

Elemental Analysis

C, 77.96; H, 8.05; N, 13.99

Medetomidine HCl (hereinafter referred to as the “target compound”), as a hypothetical drug molecule, may have specific pharmacological activities such as analgesia, sedation, or anti anxiety. To obtain this compound, we need to start from readily available raw materials, gradually construct its molecular skeleton through a series of chemical reactions, and introduce necessary functional groups. In this synthesis route, we will use 1- (2,3-dimethylphenyl) ethanone (referred to as the “ketone raw material”) as the key starting material, and synthesize the target compound through steps such as epoxidation, isomerization, and van Leesen reaction.

Synthesis of raw material 1- (2, 3-dimethylphenyl) ethanone

Synthesis route using 2,3-dimethylbenzoic acid as raw material

Step 1: Acyl chloride

Reaction principle: Benzoic acid reacts with thionyl chloride (SOCl2) or oxalyl chloride under acidic conditions to generate the corresponding acyl chloride.

Chemical equation: C6H3 (CH3) 2COOH+SOCl2 → C6H3 (CH3) 2COCl+HCl+SO2

Reaction conditions: Anhydrous solvents (such as dichloromethane, chloroform, etc.) are usually used, and a small amount of catalyst (such as DMF) is added to promote the reaction. The reaction temperature is generally between 0 ° C and room temperature.

Caution: Acyl chlorides are easily hydrolyzed, and the reaction system should be kept dry and carried out under inert gas protection.

Step 2: Nucleophilic substitution reaction

Reaction principle: Acyl chloride undergoes a substitution reaction with nucleophilic reagents such as sodium alcoholate to form esters or ketones.

Chemical equation: C6H3 (CH3) 2COCl+CH3CH2ONa → C6H3 (CH3) 2COCH2CH3+NaCl

Reaction conditions: Under alkaline conditions, commonly used solvents are ethanol or ether. The reaction temperature depends on specific conditions, but generally does not exceed the boiling point of the solvent.

Step 3: Hydrolysis reaction

Reaction principle: Esters are hydrolyzed under acidic or alkaline conditions to produce the corresponding alcohols or carboxylic acids and their salts.

Chemical equation: C6H3 (CH3) 2COCH2CH3+H2O → C6H3 (CH3) 2COCH3+CH3CH2OH

Reaction conditions: Dilute sulfuric acid or hydrochloric acid is commonly used under acidic conditions, while sodium hydroxide or potassium hydroxide is commonly used under alkaline conditions. The reaction temperature is generally from room temperature to reflux temperature.

Total yield: The three-step total yield is 71.7%, indicating that this route has a high synthesis efficiency.

Synthesis route using 2,3-dimethylaniline as raw material (low yield alternative)

Due to the low yield of this route (13.9%), it is only briefly mentioned here for reference.

Steps: diazotization, coupling, hydrolysis.

Description: Firstly, 2,3-dimethylaniline undergoes diazotization reaction to generate diazonium salts; Then, diazonium salts react with appropriate coupling agents (such as olefins, aromatics, etc.) to form intermediates; Finally, the intermediate was hydrolyzed to obtain 1- (2,3-dimethylphenyl) ethanone.

Synthesis of key intermediate 2- (2,3-dimethylphenyl) -2-methylepichlorohydrin

Reaction principle: Ketone raw materials undergo epoxidation reaction under the action of epoxidation reagents to generate epichlorohydrin compounds.

C6H3 (CH3) 2COCH3+(CH3) 3S+HSO4- → 2- (2,3-dimethylphenyl) -2-methylepichlorohydrin+byproduct

Reaction conditions: Use (CH3) 3S+HSO4- as the epoxidation reagent and carry out the reaction in an appropriate solvent (such as dichloromethane, chloroform, etc.). The reaction temperature needs to be optimized according to specific conditions to ensure high yield and low by-product generation.

Optimization direction: By using methods such as simplex optimization or response surface methodology, optimize parameters such as material ratio, reaction temperature, and reaction time to improve the yield of epoxidation.

Synthesis of the target compound medetomidine hCl

Reaction principle: Epoxy propane compounds can undergo isomerization reaction under appropriate conditions, forming compounds with different carbon skeleton structures. However, in the synthetic pathway of metoclopramide hydrochloride (hypothetical compound), directly isomerizing 2- (2,3-dimethylphenyl) -2-methylepichlorohydrin to the specific structure of the target compound may not be the most direct or effective method. Therefore, this step may require the combination of other reaction types, such as rearrangement, reduction, substitution, etc., to gradually construct the skeleton of the target compound.

To simplify the discussion, we assume that there are one or more intermediate steps through which epichlorohydrin is converted into an intermediate that is closer to the structure of the target compound. These steps may include.

(1) Ring opening reaction:

Epoxypropane opens its ring under acidic or alkaline conditions to form the corresponding alcohol or aldehyde compounds. This step may not be necessary, but it can provide convenience for subsequent functional group conversion.

(2) Functional group conversion:

Through reactions such as oxidation, reduction, and substitution, the ring opened compound is converted into an intermediate containing the desired functional group of the target compound. For example, aldehyde groups can be reduced to alcohol groups or oxidized to carboxyl groups; Functional groups such as halogens and nitro groups can also be introduced through substitution reactions.

(3) Cyclization reaction:

Under appropriate conditions, linear or branched intermediates are cyclized to reconstruct a cyclic structure. This step is one of the key steps in constructing the skeleton of the target compound.

(4) Van Leesen reaction or similar reaction:

If the target compound contains specific heterocyclic structures (such as imidazole ring, pyridine ring, etc.), it may need to be constructed through van Leesen reaction or similar heterocyclic synthesis reaction. The van Leesen reaction typically involves the condensation of ketone compounds with ammonia or amine compounds, followed by cyclization to form heterocycles. However, in the synthesis of metoclopramide hydrochloride, the specific reaction type and conditions may need to be adjusted according to the specific structure of the target compound.

(5) Salt formation reaction:

Finally, the heterocyclic compound containing basic nitrogen atoms is reacted with inorganic acids such as hydrochloric acid to generate the corresponding hydrochloride salt, namely the target compound metoclopramide hydrochloride.

Synthesis is a complex and intricate process that involves a combination of multiple steps and reaction types. By selecting raw materials reasonably, optimizing reaction conditions, and introducing efficient catalysts and separation and purification techniques, the efficient synthesis of the target compound can be achieved. The above steps are only a simplified synthesis pathway example, and in the actual synthesis process, adjustments and optimizations may need to be made based on the specific structure and properties of the target compound. In addition, each step of the reaction requires strict control of reaction conditions (such as temperature, pressure, solvent, catalyst, etc.) to ensure efficient reaction and purity of the product.

Medetomidine HCl is a multifunctional drug, which is widely used in Veterinary medicine and human medicine.

1. sedatives:

it is often used as a sedative in veterinary clinical practice. Its sedative effect is very strong and has the characteristics of rapid onset and long duration. By stimulating the central nervous system α 2 Adrenergic receptor, it can inhibit neuronal discharge, thus producing sedative effect. It is usually used for animal surgical procedures, diagnostic tests, and other situations where animals are required to remain stationary.

2. Analgesics:

it has significant analgesic effects and can alleviate pain in animals or humans. It is activated by α Adrenergic receptor inhibits pain conduction in the central nervous system, thereby reducing pain. it is widely used for analgesia management before, during and after surgery, and can also be used to treat acute or Chronic pain caused by trauma, disease or other reasons.

3. Anesthetic aids:

it is often used as an adjuvant of Narcotic, and is used in combination with other anesthetics. It can enhance the effect of Narcotic and reduce the required anesthetic dose, thus reducing the anesthetic risk and adverse reactions. Medetomidine Hydrochloride can be used for the management of anesthesia status during surgical anesthesia, maintenance of anesthesia, and monitoring.

Medetomidine HCl is a selective α2 – adrenoceptor ( α2 – adrenoceptor ) agonist with Ki of 1.08 nM, which is 1620 times higher than that for α1 – adrenoceptor. Medetomidine is a selective α2 – adrenoreceptor agonist with a Ki of 1.08 nM, which is 1620 times higher than that of α1 – adrenoreceptor, and has weak or no binding to other neurotransmitter receptors.

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