32795-44-1

Basic information

• Product Name: N-ACETYLPROCAINAMIDE
• Synonyms: 4-(acetylamino)-n-(2-(diethylamino)ethyl)-benzamid;4-(acetylamino)-n-[2-(diethylamino)ethyl]-benzamid;4’-((2-(diethylamino)ethyl)carbamoyl)-acetanilid;4’-((2-(diethylamino)ethyl)carbamoyl)acetanilide;acecainide;acekainid;n-acetyloprokainamid;N-ACETYLPROCAINAMIDE
• CAS NO: 32795-44-1
• Molecular Formula: C₁₅H₂₃N₃O₂
• Molecular Weight: 277.36
• EINECS: 251-831-2
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks;TINDAMAX
• Mol File: 32795-44-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 138-140 °C(lit.)
• Boiling Point: 500°Cat760mmHg
• Flash Point: 256.2°C
• Appearance: /
• Density: 1.097g/cm³
• Vapor Pressure: 3.93E-10mmHg at 25°C
• Storage Temp.: -20°C
• Solubility: soluble1%, clear, colorless to faintly yellow (1N HCl)
• PKA: 14.54±0.46(Predicted)
• Merck: 13,20
• CAS DataBase Reference: N-ACETYLPROCAINAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYLPROCAINAMIDE(32795-44-1)
• EPA Substance Registry System: N-ACETYLPROCAINAMIDE(32795-44-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 3249
• WGK Germany: 3
• RTECS: AE1974350
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 32795-44-1(Hazardous Substances Data)

Usage

Originator

Acecainide ,ZYF Pharm Chemical

Uses

Different sources of media describe the Uses of 32795-44-1 differently. You can refer to the following data:
1. antiprotozoal
2. N-acetylprocainamide (NAPA) was used as a model drug in the study of establishing a quantitative approach to predict the renal clearances of basic drugs using N-1-methylnicotinamide (NMN).

Definition

ChEBI: A benzamide obtained via formal condensation of 4-acetamidobenzoic acid and 2-(diethylamino)ethylamine.

Manufacturing Process

1.0 g of p-amino-N-(2-diethylaminoethyl)benzamide is dissolved in chloroform. A few ice cubes are added to the solution. Acetyl chloride is added dropwise with stirring until no more white precipitate forms; the latter is separated by filtering under suction. The precipitate is washed with cold acetone and dried overnight in a vacuum oven at room temperature. The product is dissolved in a minimum amount of hot isopropanol and allowed to precipitate in the cold. The p-acetamido-N-(2-diethylaminoethyl)benzamide hydrochloride, is recrystallized a second time from hot isopropanol, melting point 190°-193°C. The free base is obtained from the hydrochloride by dissolving the latter in water, adjusting the pH to greater than 10 with dilute sodium hydroxide, and adding an equal volume of benzene. After shaking in a separatory funnel, the benzene layer is recovered and evaporated to dryness. So the p-acetamido-N- (2-diethylaminoethyl)benzamide is obtained.

Therapeutic Function

Antiarrhythmic

General Description

The relaxant effects of N-acetylprocainamide on bovine tracheal smooth muscle was studied.

InChI:InChI=1/C15H23N3O2.ClH/c1-4-18(5-2)11-10-16-15(20)13-6-8-14(9-7-13)17-12(3)19;/h6-9H,4-5,10-11H2,1-3H3,(H,16,20)(H,17,19);1H

Upstream product

• 614-39-1 procainamide hydrochloride 
• 75-36-5 acetyl chloride 
• 122-85-0 para-acetamidobenzaldehyde 
• 100-36-7 N,N-diethylethylenediamine 
• 201230-82-2 carbon monoxide 
• 103-88-8 4-bromoacetanilide 
• 103-89-9 4-Methylacetanilide 
• 16375-88-5 N-(4-hydroxymethylphenyl)acetamide 

Relevant articles and documents

Two-step continuous flow synthesis of amide via oxidative amidation of methylarene

A green and efficient method for the synthesis of amides has been developed through oxidative amidation between methylarenes with amines in a two-step continuous flow system. This method integrates methylarene oxidation and amide formation into a single operation which is usually accomplished separately. Oxidation with tert-butyl hydroperoxide (TBHP) as “green” oxidant, the synthesis of amides under mild reaction conditions in continuous flow system and the utilization of methylarenes as starting material make this methodology novel and environment friendly. The practical value of this method is highlighted through the synthesis of high-profile pharmaceutical agents, acetylprocainamide.

Iron-catalyzed direct synthesis of amides from methylarenes

An efficient, green and first catalytic process has been developed for the direct synthesis of amides from readily available petroleum by-products (methylarenes) and amines using an iron catalyst. In this new catalytic reaction, the methyl group of the me

Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides

A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide.