748-44-7

Basic information

• Product Name: Acoxatrine
• Synonyms: Acoxatrine;N-[[1-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-4-phenyl-4-piperidyl]methyl]acetamide;N-[[1-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-4-phenylpiperidin-4-yl]methyl]acetamide;N-[[1-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-4-phenyl-piperidin-4-yl]methyl]ethanamide
• CAS NO: 748-44-7
• Molecular Formula: C23H28N2O3
• Molecular Weight: 380.485
• Mol File: 748-44-7.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 565.7°C at 760 mmHg
• Flash Point: 295.9°C
• Appearance: /
• Density: 1.145g/cm³
• Vapor Pressure: 8.13E-13mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: Acoxatrine(CAS DataBase Reference)
• NIST Chemistry Reference: Acoxatrine(748-44-7)
• EPA Substance Registry System: Acoxatrine(748-44-7)

Safety Data

• Hazardous Substances Data: 748-44-7(Hazardous Substances Data)

Usage

Originator

Acoxatrine ,ZYF Pharm Chemical

Manufacturing Process

To a solution of 11.5 parts lithium aluminum hydride in 100 parts tetrahydrofurane is added dropwise a solution of 94 parts DL-1-cyano-4- phenyl-piperidine in 240 parts tetrahydrofurane, at a temperature of about 45°C. After the addition is complete, the reaction mixture is stirred first at the same temperature for 3 h and 30 min and then refluxed for 1 h. The whole is decomposed by successive addition of 12 parts water, 9 parts sodium hydroxide 20% and 50 parts water. The mixture is filtered from inorganic matter. The filter-cake is washed with tetrahydrofurane and the combined filtrates are evaporated. The oily residue is dissolved in 240 parts 2-propanol and to this solution are added about 60 parts concentrated hydrochloric acid. After keeping at room temperature, the precipitated salt is filtered off, washed with 2-propanol and dried, yielding DL-4-(amino-methyl)-1-[1,4- benzodioxanyl)methyl]-4-phenylpiperidine dihydrochloride; melting point 272°-278°C as a white amorphous powder. From 4.1 parts DL-4-(aminomethyl)-1-[2-(1,4-benzodioxanyl)methyl]-4- phenylpiperidine dihydrochloride, the free base is liberated in the usual manner and extracted with chloroform. The organic layer is separated, dried and evaporated. The DL-4-(aminomethyl)-1-[2-(1,4-benzodioxanyl)methyl]-4- phenylpiperidine obtained is dissolved in 128 parts anhydrous chloroform. This solution is cooled to 5°C and there is added dropwise a solution of 1.6 parts acetylchloride in 7 parts anhydrous chloroform (exothermic reaction). The reaction mixture is stirred over night at room temperature and then alkalized with about 25 parts sodium hydroxide 20% at a temperature of 20°C. The aqueous layer is separated and extracted twice with chloroform. The combined organic layers are washed with water, dried over magnesium sulfate, filtered and evaporated. The oily residue is dissolved in a mixture of 40 parts acetone and 20 parts diisopropyl ether and evaporated again. The solid residue is triturated in diisopropylether, yielding DL-4-(N-acetylaminomethyl)-1-[2-(1,4- benzodioxanyl)-methyl]-4-phenylpiperidine; melting point 140°-141.1°C, as a white microcrystalline powder.

Therapeutic Function

Vasodilator, Antihypertensive

InChI:InChI=1/C23H28N2O3/c1-18(26)24-17-23(19-7-3-2-4-8-19)11-13-25(14-12-23)15-20-16-27-21-9-5-6-10-22(21)28-20/h2-10,20H,11-17H2,1H3,(H,24,26)