75558-90-6

Basic information

• Product Name: Amperozide
• Synonyms: Amperozide;4-[4,4-Bis(4-fluorophenyl)butyl]-N-ethyl-1-piperazinecarboxamide;FG-5606;4-[4,4-bis(4-fluorophenyl)butyl]-N-ethylpiperazine-1-carboxamide
• CAS NO: 75558-90-6
• Molecular Formula: C23H29F2N3O
• Molecular Weight: 401.498
• Product Categories: Serotonin receptor
• Mol File: 75558-90-6.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 579.5 °C at 760 mmHg
• Flash Point: 304.3 °C
• Appearance: /
• Density: 1.151 g/cm³
• Vapor Pressure: 2.01E-13mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Store at +4°C
• PKA: 14.59±0.20(Predicted)
• CAS DataBase Reference: Amperozide(CAS DataBase Reference)
• NIST Chemistry Reference: Amperozide(75558-90-6)
• EPA Substance Registry System: Amperozide(75558-90-6)

Safety Data

• Hazardous Substances Data: 75558-90-6(Hazardous Substances Data)

Usage

Originator

Amperozide,Ferrosan

Manufacturing Process

(1). A stirred mixture of 4.7 g (0.03 mole) of N'-ethyl-1- piperazinecarboxamide, 10.1 g (0.036 mole) of 4-chloro-1,1-(di-pfluorophenyl) butane, 5.0 g of sodium bicarbonate and 10 ml of ethanol was heated at reflux for 60 hours. 50 ml of water was added. The mixture was extracted twice with ether. The combined extracts were dried over sodium sulfate and concentrated. The residue was dissolved in ethanol-ether and the hydrochloride was precipitated with hydrogen chloride in ethanol. The solid was collected by filtration and recrystallised from 2-butanone-isopropanol 4:1 to give 6.4 g of N'-ethyl-4-[4,4-(di-p-fluorophenyl)butyl]-1- piperazinecarboxamide hydrochloride. Melting point 177-178°C. (2). A stirred mixture of 9.9 g (0.03 mole) of 1-[4,4-(di-pfluorophenyl) butyl]piperazine, 5,0 g (0,03 mole) of phenyl N-ethylcarbamate, 6,6 g of potassium carbonate and 100 ml of toluene was heated at reflux for 45 minutes. The mixture was filtered and the solvent was removed. The residual oil was dissolved in ethanol-ether and the hydrochloride was precipitated with hydrogen chloride in ethanol. The solid was collected by filtration and recrystallized from 2-butanone-isopropanol 4:1 to give 6.8 g of N'-ethyl-4-[4,4-(di-p-fluorophenyl)butyl]-1-piperazinecarboxamide hydrochloride. Melting point 177-178°C.

Therapeutic Function

Anti-aggressive, Antiarrhythmic

Biological Activity

Atypical antipsychotic that displays high affinity for 5-HT 2 receptors (K i = 26 nM) and low affinity for D 2 receptors. Supresses ethanol drinking in genetically ethanol-preferring rats.

InChI:InChI=1/C23H29F2N3O/c1-2-26-23(29)28-16-14-27(15-17-28)13-3-4-22(18-5-9-20(24)10-6-18)19-7-11-21(25)12-8-19/h5-12,22H,2-4,13-17H2,1H3,(H,26,29)