103146-26-5

Basic information

• Product Name: 4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hydrobromide
• Synonyms: 4-[(4-DIMETHYLAMINO)-1-(4-FLUORO PHENYL)-1-HYDROXYBUTYL]-3-HYDROXY-METHYL BENZONITRILE HYDROBROMIDE;4-[4-(DIMETHYLAMINO)-1-(4-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-(HYDROXYMETHYL)-BENZONITRILE, MONOHYDROBROMIDE;4-[4-(Dimethylamino)-1-(4-Fluorophenyl)-1-HydroxyButyl]-3-(Hydroxymethyl)-Benzon;Benzonitrile, 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)-, monohydrobromide;4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile hydrobromid;Citadiol HBr;4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hydrobromide###4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile;4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile hydrobro
• CAS NO: 103146-26-5
• Molecular Formula: BrH*C₂₀H₂₃FN₂O₂
• Molecular Weight: 423.32
• EINECS: 1592732-453-0
• Product Categories: API intermediates
• Mol File: 103146-26-5.mol

Chemical Properties

• Melting Point: 201-205 °C(lit.)
• Boiling Point: 561.6 °C at 760 mmHg
• Flash Point: 293.5 °C
• Appearance: White solid
• Vapor Pressure: 1.89E-13mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hydrobromide(103146-26-5)
• EPA Substance Registry System: 4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hydrobromide(103146-26-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 103146-26-5(Hazardous Substances Data)

Usage

Uses

Citadiol Hydrobromide is a precursor of Citalopram (C505000), an antidepressant.

InChI:InChI=1/C20H23FN2O2.BrH/c1-23(2)11-3-10-20(25,17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24;/h4-9,12,24-25H,3,10-11,14H2,1-2H3;1H

Upstream product

• 19070-16-7 3-(N,N-dimethylamino)propylmagnesium chloride 
• 82104-74-3 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile 
• 352-13-6 4-flourophenylmagnesium bromide 
• 109-54-6 3-(Dimethylamino)propyl chloride 
• 103146-25-4 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile 

Downstream Products

• 103146-25-4 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile 
• 59729-32-7 citalopram hydrobromide 
• 128173-53-5 4-(1S)-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile (+)-di-(p-toluoyl)tartaric acid 
• 128196-01-0 escitalopram 
• 219861-08-2 escitalopram oxalate 

Relevant articles and documents

PROCESS FOR PRODUCING HYDROBROMIDE OF DIOL COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)-benzonitrile hydrobromide with a high purity and a high isolation yield. SOLUTION: Provided is a process for producing 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)-benzonitrile hydrobromide characterized in bringing 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)-benzonitrile and hydrogen bromide into contact in a mixed solvent of an ester-based solvent and water. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

METHOD OF PRODUCING CITALOPRAM DIOL COMPOUND

PROBLEM TO BE SOLVED: To provide a method of producing citalopram diol in a high purity and a high yield. SOLUTION: A production method for obtaining 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)-benzonitrile by reacting 5-cyanophtalide with 4-magnesiumbromidefluorobenzene and 3-magnesiumchloride-N,N-dimethyl-1-propaneamine includes: a process of obtaining a solution of 4-magnesiumbromidefluorobenzene using less than 1 mol of magnesium to 1 mol of 4-bromofluorobenzene in an organic solvent; and a process of reacting less than 1 mol magnesium with 1 mol of 3-chloro-N,N-dimethyl-1-propanamine in an organic solvent to obtain a solution of 3-magnesiumchloride-N,N-dimethyl-1-propaneamine. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Preparation method of citalopram intermediate

The invention provides a preparation method of a citalopram intermediate, and belongs to the technical field of pharmaceuticals. In the method, 2-methyltetrahydrofuran is taken as a reaction solvent. Under the protection of nitrogen, a 4-fluorophenylmagnesium bromide solution Grignard reagent, 5-cyanophthalein and a N,N-dimethylpropyl magnesium chloride Grignard reagent are taken as raw materials. A reaction is carried out to synthesize 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrilehydrobromide. The method is characterized by high yield and high purity, and is suitable for industrial production.

PREPARATION OF CITALOPRAM AND SALTS THEREOF

Process for the preparation of citalopram and its salts, comprising reacting magnesium (5-cyano-2-(4-fluorobenzoyl)phenyl)methanolate bromide with 3-N,N-dimethylaminopropyl magnesium halide in a mixture of solvents, obtaining a diol intermediate in the form of its acid addition salt, and reacting the acid addition salt with sulfuric acid in an aqueous medium.