442-03-5

Basic information

• Product Name: Anisopirol
• Synonyms: Anisopirol;1-(4-fluorophenyl)-4-[4-(2-methoxyphenyl)piperazin-1-yl]butan-1-ol
• CAS NO: 442-03-5
• Molecular Formula: C21H27FN2O2
• Molecular Weight: 358.454
• Mol File: 442-03-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 514.2°C at 760 mmHg
• Flash Point: 264.8°C
• Appearance: /
• Density: 1.154g/cm³
• Vapor Pressure: 2.14E-11mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: Anisopirol(CAS DataBase Reference)
• NIST Chemistry Reference: Anisopirol(442-03-5)
• EPA Substance Registry System: Anisopirol(442-03-5)

Safety Data

• Hazardous Substances Data: 442-03-5(Hazardous Substances Data)

Usage

Originator

Anisopirol,ZYF Pharm Chemical

Manufacturing Process

A mixture of 6.6 parts of γ-chloro-4-fluorobutyrophenone and 12.5 parts of 1- (2-methoxyphenyl)piperazine, heated for 10 hours at a temperature of 110°C. The reaction mixture is treated with 800 parts of ether and fiItered. The ether layer is washed with water, dried over anhydrous potassium carbonate and filtered, whereupon hydrogen chloride gas is introduced into the solution. The precipitate is collected on a filter and dissolved in a mixture of 240 parts of 2- propanol and 80 parts of acetone to yield 1-[γ-(4-fluorobenzoyl)propyl]-4-(2- methoxyphenyl)piperazine hydrochloride. This monohydrochloride is collected on a filter and dissolved in 240 parts of 2-propanol. Anhydrous, gaseous hydrogen chloride is passed through the solution. On cooling, the 1-[γ-(4- fluorobenzoyl)propyl]-4-(2-methoxyphenyl)piperazine hydrochloride precipitates. A second crop of product is obtained by passing hydrogen chloride gas through the solution of mother liquors. The pale-brown, amorphous powder is collected on a filter and found to melt at about 205°-205.5°C. This salt is dissolved in water and treated with sodium hydroxide. The precipitated base is recovered by filtration and recrystallized from diisopropylether. The white crystals melt about 67.5°-68.5°C. By dissolving 4 parts of 1-[γ-(4-fluorobenzoyl)propyl]-4-(2-methoxyphenyl) piperazine dihydrochloride in 800 parts of water, rendering alkaline, extracting with 400 parts of ether, drying over calcium chloride, filtering, and evaporating the resulting solution, the free base of 1-[γ-(4-fluorobenzoyl) propyl]-4-(2-methoxyphenyl)piperazine is obtained. This product is dissolved in 120 parts of absolute ethanol and 0.03 part of sodium borohydride is added portionwise at 35°C. After decomposition with 150 parts of 1 N hydrochloric acid, the mixture is diluted with 500 parts of water, made alkaline with 4 N sodium hydroxide, and further diluted to a volume of 1,000 parts. Upon cooling for 4 hours at 0°C the precipitate formed is filtered, dried, and recrystallized from diisopropyl ether to yield 1-(4-fluorophenyl)-4-[4-(2- methoxyphenyl)piperazine]-1-butanol (anisopirol). The white granular powder of this compound has a melting point of about 105°-106°C.

Therapeutic Function

Neuroleptic

InChI:InChI=1/C21H27FN2O2/c1-26-21-7-3-2-5-19(21)24-15-13-23(14-16-24)12-4-6-20(25)17-8-10-18(22)11-9-17/h2-3,5,7-11,20,25H,4,6,12-16H2,1H3

Upstream product

• 1402042-57-2 1-[4-(benzyloxy)-4-(4-fluorophenyl)-butyl]-4-(2-methoxyphenyl)piperazine 
• 1402042-56-1 4-(benzyloxy)-4-(4-fluorophenyl)-butanal 
• 1402042-55-0 4-(benzyloxy)-4-(4-fluorophenyl)-butan-1-ol 
• 1143515-07-4 1-[1-(benzyloxy)-but-3-enyl]-4-fluorobenzene 
• 86718-78-7 1-(4-fluorophenyl)-3-buten-1-ol 
• 459-57-4 4-fluorobenzaldehyde 

Relevant articles and documents

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