3858-89-7

Basic information

• Product Name: Chloroprocaine hydrochloride
• Synonyms: 2-diethylaminoethyl 4-amino-2-chlorobenzoate hydrochloride;chloroprocaine hydrochloride;CHLOROPROCAINE HYDROCHLORIDE (200 MG);2-chloroprocainehydrochloride;4-amino-2-chlorobenzoicacid2-(diethylamino)ethylesterhydrochloride;4-Amino-2-Chlorobenzoicacid2-diethylaminoe-thylesterhydrochloride;benzoicacid,4-amino-2-chloro-,2-(diethylamino)ethylester,hydrochloride;nesacainehydrochloride
• CAS NO: 3858-89-7
• Molecular Formula: C₁₃H₁₉ClN₂O₂*ClH
• Molecular Weight: 307.2161
• EINECS: 223-371-2
• Product Categories: Inhibitors
• Mol File: 3858-89-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 176-178° (microstage)
• Boiling Point: 402.6 °C at 760 mmHg
• Flash Point: 197.3 °C
• Appearance: White crystalline powder
• Vapor Pressure: 1.08E-06mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Chloroprocaine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Chloroprocaine hydrochloride(3858-89-7)
• EPA Substance Registry System: Chloroprocaine hydrochloride(3858-89-7)

Safety Data

• Hazardous Substances Data: 3858-89-7(Hazardous Substances Data)

Usage

Chemical Properties

crystalline solid

Originator

Nesacaine,Astra,US,1956

Uses

Different sources of media describe the Uses of 3858-89-7 differently. You can refer to the following data:
1. Chloroprocaine Hydrochloride is a local anaesthetic compound showing similar effects to Lidocaine.
2. Anesthetic (local).

Definition

ChEBI: The monohydrochloride salt of chloroprocaine. Used as a local anaesthetic, particularly for oral surgery, it has the advantage over lidocaine of constricting blood vessels, so reducing bleeding.

Manufacturing Process

In the first step, 2-chloro-4-aminobenzoyl chloride hydrochloride is prepared by refluxing a mixture of 25 cc of purified thionyl chloride and 10 g of 2- chloro-4-aminobenzoic acid until all of the solid has gone into solution. To the cooled solution is added 150 cc of dry ethyl ether. A brisk stream of dry hydrogen chloride is passed into the solution until the precipitation of 2- chloro-4-aminobenzoylchloride hydrochloride is complete. The acyl halide is removed by filtration and dried in a vacuum desiccator. In the second step, the diethylaminoethyl 2-chloro-4-aminobenzoate hydrochloride is prepared by refluxing equimolar proportions of the hydrochloride of beta-diethylaminoethanol in a suitable inert solvent such as a mixture of dry toluene and tetrachloroethane and the hydrochloride of 2- chloro-4-aminobenzoyl chloride until the reaction as indicated by the cessation of hydrogen chloride evolution is complete. The supernatant solvents are decanted from the reaction product which can be conveniently purified by crystallization from absolute ethanol.An alternative purification can be effected by dissolving the reaction product in water. The ester base is liberated by rendering the clarified aqueous solution alkaline. Removal of the base from the alkaline solution is achieved by extraction with a suitable solvent such as benzene or ether. The pure hydrochloride of diethylaminoethyl 2-chloro-4-aminobenzoate is then precipitated from the dried extract by the addition of dry hydrogen chloride. After removal by filtration and recrystallization from ethanol it is found to have a melting point of 173° to 174°C.

Therapeutic Function

Local anesthetic

InChI:InChI=1/C13H19ClN2O2.ClH/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14;/h5-6,9H,3-4,7-8,15H2,1-2H3;1H

Upstream product

• 2457-76-3 4-amino-2-chlorobenzoic acid 
• 14426-20-1 N,N-diethylethanolammonium chloride 
• 10367-96-1 2-(diethylamino)ethyl 2-chloro-4-nitrobenzoate 

Relevant articles and documents

Preparation method of chloroprocaine hydrochloride

The invention belongs to the technical field of organic drug synthesis and particularly relates to a preparation method of chloroprocaine. The preparation method includes the steps that 1, 2-chloro-4-nitrobenzoic acid and 2-diethylaminoethanol reaction raw materials are added into a xylene reaction solvent, para-toluenesulfonic acid or immobilized liquid acid or faintly acid metal salt is added to serve as a catalyst, heating is conducted till reflux is achieved, a reaction is carried out for a certain period of time, aftertreatment is carried out, and a water solution of nitrochlor cain is obtained; 2, ammonium chloride and iron powder are added into the water solution of nitrochlor cain, a heating reaction is carried out, aftertreatment is carried out, and crude chloroprocaine hydrochloride is obtained; refining is carried out, and chloroprocaine hydrochloride is obtained. The direct esterification reaction time is short, the production period is shortened by 30% or above, the total yield of the finished product is larger than 30%, and energy consumption is reduced by 25% or above. The content of chloroprocaine hydrochloride is not smaller than 99.0%, the content of related substances is not larger than 1.0%, and the content of a residual solvent (dimethylbenzene) does not exceed 0.1%. The preparation method is suitable for industrial production.