3'-Chloropropiophenone CAS 34841-35-5
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- Appearance: White powder
- Assay: 99. 0%min
- Stock: In stock
- Sample: Available
- Zhishang Chemical: 3′-Chloropropiophenone Supplement
3'-Chloropropiophenone: The Complete Guide
3'-Chloropropiophenone for Sale
Basic Info of 3'-Chloropropiophenone
3-CHLORO PROPIOPHENONE; 3-Chloropropiophenone
Pharmaceutical raw materials; Organic raw materials
What is 3'-Chloropropiophenone?
3-Chloropropiophenone is a key intermediate in the synthesis of bupropion hydrochloride, dapoxetine and maraviroc. Bupropion hydrochloride is an antidepressant, which is a blocker of weak neuronal absorption of serotonin and norepinephrine. Bupropion can also be used as an adjunctive treatment for smoking cessation, viral infections, or sexual dysfunction.
Bupropion is a new type of antidepressant, and it can also play a smoking cessation effect by blocking the uptake of dopamine, serotonin and norepinephrine by nerves. It is widely used in clinical practice. The key intermediate of ketone. At present, the traditional process of industrial production of m-chloropropiophenone at home and abroad is that 1,2-dichloroethane is used as a solvent, aluminum trichloride is used as a catalyst, and Propiophenone is reacted with chlorine to obtain m-chloropropiophenone, but 1,2-dichloroethyl Alkane is flammable, highly toxic, and highly carcinogenic; aluminum trichloride vapor is irritating to the respiratory tract and causes bronchitis, and has a strong irritating effect on the skin and mucous membranes, and a large amount of acidic wastewater is produced during production. Industrial production is very difficult. Therefore, to seek advanced technology and low production cost, it is imperative to develop the green production technology of m-chloropropiophenone.
Reported in the patent, in 1,2-dichloroethane as solvent, under the catalysis of anhydrous aluminum trichloride, Propiophenone and chlorine generate chlorination reaction to synthesize m-chloropropiophenone, and the yield is 89%. Because this method uses a large amount of 1,2-dichloroethane as the reaction solvent during the synthesis, long-term contact and use will cause great harm to the human body. The pharmaceutical factory has banned the use of m-chloropropiophenone containing dichloroethane residues. As a raw material for the production of antidepressant bupropion.
- 3′-Chloropropiophenone is a key intermediate in the synthesis of bupropion hydrochloride, dapoxetine and maraviroc. Mainly used in laboratory organic synthesis and chemical production process.
- 3′-Chloropropiophenone is a reagent used for vinyl, alkylation and dienylation of ketones. It is also used to prepare thiazine derivatives with antibacterial activity.
- 3′- Chlorophenyl acetone has been used to prepare 1- (3-chlorophenyl) – 1-phenyl-1-propanol.
- 3′- Chlorophenyl acetone can be used as reactant (s) – 3-chloro-1-phenylpropanol was synthesized by biocatalytic asymmetric reduction.
1- (3-chlorophenyl) – 1-phenyl-1-propanol is phenylated with diphenylzinc in the presence of dihydroxy bis (sulfonamide) ligand.
(S) – dapoxetine, a selective serotonin reuptake inhibitor.
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Application of 3'-Chloropropiophenone
3′-Chlorophenylpropanol, as an important intermediate in the synthesis of dapoxetine, plays a key role in the cost and quality of the entire drug. About the synthesis report of R-3′-chlorophenylpropanol, mainly focus on taking 3′-chloropropiophenone as raw material, through reducing agent, synthesizes target product.
The target compound is synthesized by using tetrahydrofuran as a solvent and a spiro boron ester compound as a catalyst. The cost of this process solvent and catalyst is relatively high. With 95% ethanol as solvent and potassium borohydride as reducing agent, the cost is low. However, the synthesized product is a mixture, which needs to be split before the target product can be formed, and the final total yield is low, resulting in high cost. DMSO is used as solvent, and chiral catalysts are not common and have high cost. The post-processing is complicated and the energy consumption is large. Using ethylene glycol dimethyl ether as solvent and sodium borohydride as reducing agent. The cost of the solvent is high, and the product is a mixture that needs to be split.
To sum up, in the synthesis technique of R-3′-chlorophenylpropanol, there are ubiquitous shortcomings such as high solvent and reducing agent cost, difficult aftertreatment, difficult control of reaction process, low selectivity, low chiral purity, etc. To sum up, the research on the synthesis process of R-3′-chlorophenylpropanol, the development of a production process with lower cost, convenient handling and better product quality, is of great significance to the synthesis of the above-mentioned drugs and the treatment of related diseases. Has a broad market prospect.
Adopt the technique of 3-chloropropiophenone to synthesize 3′-chlorophenylpropanol, the concrete steps are as follows:
1) Add 3′-chloropropiophenone and L-prolinol successively to 95% ethanol and stir;
2) Cool down after the reaction solution is completely dissolved;
3) Add potassium borohydride to the reaction solution in batches, and keep the temperature after adding;
4) After the reaction solution is heated to reflux for reaction, the reaction solution is concentrated under reduced pressure;
5) Add n-hexane to the reaction solution, heat, and then add activated carbon to decolorize by heat preservation;
6) Filter the reaction solution, rinse the filter cake with 500-700ml of n-hexane, and collect the filtrate;
7) The filtrate is crystallized and filtered, and the filter cake is rinsed once with 300-500ml of n-hexane, and dried in vacuum to obtain 3′-chlorophenylpropanol.
Preparation of 3'-Chloropropiophenone
Adopt m-aminopropiophenone and sodium nitrite to obtain after diazotization and chlorination, and the mol ratio between m-aminopropiophenone and sodium nitrite is 1: 1～1: 1.2.
The specific operation steps are:
Add m-aminobenzophenone and an appropriate amount of hydrochloric acid into the reaction kettle, stir and cool to 0 °C, drop an aqueous solution of sodium nitrite, control the temperature at 0 to 5 °C, and use starch potassium iodide test paper to detect the presence of excess nitrous acid. , the diazonium salt solution was added to the pre-prepared cuprous chloride solution that had been cooled to 0 °C to obtain the crude 3′-chloropropiophenone, which was washed twice with hydrochloric acid and water, and then washed with 5% sodium carbonate. The solution is washed, finally washed with water, dried and distilled under reduced pressure to obtain a product with a yield of about 60.5% and a content of 90% to 95%.