847063-13-2

Usage

Uses

Used in Pharmaceutical Industry:
1-[[2-(4-Chlorophenyl)ethyl]amino]-2-hydroxypropane is used as a key intermediate in the synthesis of lorcaserin, a medication used for weight management in obese individuals. Its unique chemical structure allows it to play a crucial role in the development of this weight loss drug, contributing to its efficacy and safety profile.

InChI:InChI=1/C11H16ClNO/c1-9(14)8-13-7-6-10-2-4-11(12)5-3-10/h2-5,9,13-14H,6-8H2,1H3

Upstream product

• 1030624-39-5 2-(4-chlorobenzyl)-5-methyl-4,5-dihydrooxazole 
• 1030624-36-2 2-(4-chlorophenyl)-N-(2-hydroxypropyl)acetamide 
• 6529-53-9 1-(2-bromoethyl)-4-chlorobenzene 
• 78-96-6 3-amino-2-propanol 
• 1878-66-6 4-chlorophenylacetic Acid 
• 156-41-2 4-chlorophenylethylamine 
• 75-56-9 methyloxirane 
• 1875-88-3 2-(4-Chlorophenyl)ethanol 
• 937-20-2 p-chlorophenacyl chloride 
• 127-00-4 1-Chloro-2-propanol 
• 140-53-4 p-chlorobenzyl cyanide 
• 32327-70-1 1-chloro-4-(2-chloroethyl)benzene 

Downstream Products

• 953789-37-2 1-[[2-(4-chlorophenyl)ethyl]amino]-2-chloropropane hydrochloride 
• 616201-80-0 (+/-)-Lorcaserin 
• 846589-98-8 Lorcaserin hydrochloride 
• 824430-78-6 bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate 
• 1030624-41-9 1-((4-chlorophenethyl)amino)propan-2-ol hydrochloride 
• 824430-78-6 2C₁₁H₁₄ClN*C₄H₆O₆ 
• 1006037-59-7 (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride 

Relevant academic research and scientific papers

Preparation method of lorcaserin intermediate

The invention relates to a preparation method of a lorcaserin intermediate 1-[2-(4-chlorphenyl)-ethylamino]-2-propanol, which specifically comprises the following steps: carrying out bromination reaction on p-chlorophenethyl alcohol serving as a starting material to obtain 4-chlorphenyl ethyl bromide, and condensing with isopropanolamine to obtain a target product. Hydrobromic acid is used as a bromination reagent, potassium carbonate is used as a condensation reaction acid-binding agent, potassium iodide is used as a condensation reaction catalyst, the yield of the technological process is high, three wastes are few, the cost is low, the operation is simple, the safety is good, and industrial production requirements are met.

Preparation method of key intermediate I of lorcaserin

The invention discloses a preparation method of a key intermediate I of lorcaserin. The preparation method comprises the steps as follows: (1) in an organic solvent A, 2,4'-dichloroacetophenone is subjected to a condensation reaction with isopropanolamine under catalysis of alkali, and 1-(4-chlorophenyl)-2-((2-hydroxypropyl)amino)ethane-1-one is obtained; (2) the 1-(4-chlorophenyl)-2-((2-hydroxypropyl)amino)ethane-1-one obtained in the step (1) is subjected to catalytic reduction with sodium borohydride and acid in a solvent B, and the key intermediate I of lorcaserin is obtained. The preparation method can synthesize the key intermediate I of lorcaserin from cheap and easily available raw materials under mild reaction conditions, has the advantages of being simple to operate, low in costand high in yield, and is energy-saving, environmentally friendly and suitable for mass production.

Preparation method for hemihydrate lorcaserin hydrochloride

The invention discloses a preparation method for hemihydrate lorcaserin hydrochloride. The preparation method comprises the following steps: (1) making a compound shown as a formula III react with ammonia to obtain a compound shown as a formula II; (2) under the protection of nitrogen gas, dissolving the compound shown as the formula II in an organic solvent, adding a hydrogen chloride solution of which the solvent is the organic solvent to salify, and adding water and cyclohexane to form a hemihydrate in order to obtain the compound shown as a formula I, wherein the organic solvent is isopropanol or 1,4-dioxane. In the preparation method disclosed by the invention, ammonium hydroxide substitutes for potassium carbonate in the prior art, so that unqualified ignition residues of a finial product caused by potassium chloride generated after salt removal can be avoided; an isopropoxide hydrochloride solution substitutes for the conventional hydrogen chloride gas, so that other impurities can be prevented from being introduced in a preparation process under the improper control of dosage and rate of the gas.

Preparation method of lorcaserin intermediate

The invention discloses a preparation method of a lorcaserin intermediate (I). According to the preparation method, p-chlorobenzyl cyanide is taken as the primary raw material, and the lorcaserin intermediate (I) is obtained after reduction reactions and condensation reactions. The primary raw materials (p-chlorobenzyl cyanide and 1-chloro-2-propanol) are cheap and easily available; raw materials, which can easily get polluted and are explosive, such as sulfoxide chloride, hydrobromic acid, borane, and the like are not used; the preparation method will not produce a large amount of wastewater and is beneficial for the environment protection; moreover, the requirements on the protection of workers are lowered, and safe production is guaranteed. The route design is novel, the raw materials are easily available, the operation is simple and feasible, and the preparation method is environment-friendly and can be applied to massive industrial production.

Lorcaserin hydrochloride hemihydrate preparation method

The invention provides a lorcaserin hydrochloride hemihydrate preparation method. The method comprises the following steps: taking ethylamine as an initial raw material, performing an aminolysis ring-opening reaction with epoxypropane, chloridizing the material, performing friedel-Crafts alkylation cyclization on the material, splitting the material with tartaric acid, dissociating tartrate and forming hydrochloride to obtain the lorcaserin hydrochloride hemihydrate. The preparation method has the characteristics of less reaction steps, mild reaction condition, low cost of a comprehensive reagent, less three wastes, simple post-treatment and simple operation, so that the preparation method has the advantage of brand new, economy and environmental protection, high efficiency, and realization of industrial production.

1 - (phenethyl-amino) propane-2-ol compound or its salt for the preparation of

The invention relates to a preparation method of 1-(phenethylamino) propane-2-alcoholic compounds or salts thereof, shown in a formula II. The preparation method comprises the following step: reacting a compound shown in a formula I with epoxy propane to generate a compound shown in the formula II. According to the preparation method provided by the invention, cheap and accessible raw materials are adopted to prepare a target compound through a one-step reaction, so that the preparation method is low in cost, simple and convenient to operate, high in yield, environmental-friendly and suitable for industrial production. The invention also relates to a preparation method of lorcaserin or salts thereof. The lorcaserin is prepared from the high-purity 1-((4-chlorophenethyl) amino) propane-2-alcohol or the salts thereof, thereby being beneficial to improvement of the quality and stability of the product.

A preparing method of (R,S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, a lorcaserin intermediate

A preparing method of (R,S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine that is a lorcaserin intermediate is disclosed. The method includes (1) dehydrating a compound 1 and a compound 2 under catalysis by boric acid to generate an amide 3, (2) reducing the intermediate 3 with a borane dimethylsulfide complex to obtain a compound 4, and (3) subjecting the compound 4 to direct ring closing with the existence of aluminum chloride to generate the lorcaserin intermediate that is the (R,S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine that is the compound 6. The method avoids use of 3,4,5-trimethoxyphenylboronic acid that is an expensive reagent, thus reducing the cost. The method avoids use of thionyl chloride so that the method is environmental friendly. A step of hydroxy chlorination is reduced so that the method is simple in process. The conversion ratio of raw materials and the total yield of reactions are increased. The yield of the compound 6 is increased from 60% in a patent to 82%. The method is suitable for industrial production. A reaction equation is shown in the description.

PROCESSES FOR THE PREPARATION OF 5-HT2C RECEPTOR AGONISTS

The present invention relates to processes and intermediates useful in the preparation of (R)-8-chloro-l-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (lorcaserin), a serotonin (5-ΗT) receptor modulator that is useful in the treatment of, for example, central nervous system disorders, such as obesity.

Processes for the Preparation of 8-Chloro-1-Methyl-2,3,4,5-Tetrahydro-1H-3-Benzazepine and Intermediates Related Thereto

The present invention provides processes, methods and intermediates for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, salts, hydrates and crystal forms thereof which are useful as serotonin (5-HT) receptor agonists for the treatment of, for example, central nervous system disorders such as obesity.

PROCESSES FOR THE PREPARATION OF INTERMEDIATES RELATED TO THE 5-HT2C AGONIST (R)-8-CHLORO-1-METHYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE

The present invention provides processes and intermediates useful in the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, a serotonin (5-HT) receptor agonist that is useful in the treatment or prophylaxis of, for example, central nervous system disorders, such as obesity.