64169-66-0

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-1-(4-FLUOROPHENYL)-PHTHALIDE is used as an antidepressant for the treatment of depression and other mood disorders. It functions by inhibiting the reuptake of serotonin in the brain, thereby increasing its availability and improving mood regulation.
As a Metabolite:
5-BROMO-1-(4-FLUOROPHENYL)-PHTHALIDE serves as a metabolite of Citalopram, which is an important aspect in understanding the drug's pharmacokinetics and pharmacodynamics. Studying its properties and effects can provide insights into the drug's mechanism of action and potential side effects.

InChI:InChI=1/C14H10BrFO/c15-11-3-6-13-10(7-11)8-17-14(13)9-1-4-12(16)5-2-9/h1-7,14H,8H2

Upstream product

• 64169-34-2 5-bromophthalide 
• 7439-95-4 magnesium 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 41377-44-0 4-Fluorbenzoesaeure-5-bromsalicyliden-hydrazon 
• 352-13-6 4-flourophenylmagnesium bromide 
• 64169-64-8 4-bromo-4'-fluoro-2-(hydroxymethyl)benzophenone 
• 64169-65-9 4-bromo-(2-hydroxymethyl)-phenyl-(4'-fluorophenyl)methanol 

Downstream Products

• 59729-33-8 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile 
• 64169-67-1 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 62498-69-5 didesmethylcitalopram 

Relevant academic research and scientific papers

Efficient synthesis of functionalized 1,3-dihydroisobenzofurans from salicylaldehydes: Application to the synthesis of escitalopram

An efficient synthesis of substituted 1,3-dihydroisobenzofurans is developed. In this novel route, o-aroylbenzaldehydes, as key intermediates, can be obtained by lead tetraacetate oxidation of N-aroylhydrazones of salicylaldehydes. The mild and general st

Novel and improved process for the preparation of citalopram

A novel process for the preparation of citalopram (1) has been described. The key intermediate 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran- 5-carbonitrile (2) of citalopram is prepared using novel intermediates. The process involves simple acylation, hydrolysis and reduction, which can be easily adapted to commercial scale.

PROCESS FOR PREPARING 5-SUBSTITUTED -1-(4-FLUOROPHENYL) -1,3-DIHYDROISOBENZOFURANS

The present invention relates to a method for preparation and isolation of hitherto unknown solid boron complex of formula (v), which are obtained when 5-substituted phthalides are reacted with a solution of 4-fluorophenylmagnesiumbromide, followed by in situ reduction and complex formation in the presence of sodiumborohydride. Such boron complexes can be conveniently filtered to remove structurally similar impurities and subsequently subjected to cyclisation reaction in acidic medium to get high pure 5-substituted phthalens, which are key starting materials for manufacturing citalopram and pharmaceutically acceptable acid addition salts.

PROCESS FOR THE PREPARATION OF HIGH PURITY CITALOPRAM AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

This invention discloses an improved process for the preparation of high purity citalopram base and its hydrobromide salt of formulae (I) and (Ia): which comprises: i. Isolation of crude citalopram base after water work up of the reaction into a non polar aromatic or dialkyl ether solvent. ii. Extraction of the citalopram base into aqueous organic acid. iii. Neutralization of acid layer with organic base to a controlled pH (7.0-8.0) iv. Extraction of the pure base into a non-polar aromatic or dialkyl ether solvent and crytallization form the same solvent after concentrating to certain volume under reduced pressure. v. Preparation of high purity citalopram hydrobromide in a non-polar aromatic or dialkyl ether solvent using 40-50 % HBr in acetic acid as HBr source and crystallizing out form the same solvent. Alternatively preparation of HBr salt in aqueous medium using aqueous HBr and crystallizing out from the same medium at 0 10 °C. vi. Recrystallization of high purity citalopram hydrobromide salt of pharmaceutically acceptable grade form a mixture of alcoholic solvent.

IMPROVED PROCESS FOR THE PREPARATION OF 5-SUBSTITUTED-1-(4--FLUOROPHENYL)-1,3-DIHYDROISOBENZOFURANS

The present invention provides a process for the preparation of a 5-substituted-l-(4-fluorophenyl)-1,3-dihydro-isobenzofuran of Formula (2), an intermediate for the manufacture of citalopram, which process comprises: (a) carrying out a Grignard reaction on a corresponding 5-substituted phthalide of Formula (3) in a co-solvent system, comprising adding (i) prepared 4-fluorophenyl magnesium halide in an ether solvent to (ii) the 5-substituted phthalide in a suitable organic co-solvent to the ether solvent, to form a corresponding 4-substituted-2-hydroxymethyl-4'-fluorobenzophenone of Formula (4); (b) carrying out a ketone reduction of the 4-substituted-2-hydroxymethyl-4'-fluorobenzophenone of Formula (4) following the Grignard reaction, to form a corresponding 4-substituted-2-hydroxymethylphenyl- 1-(4-fluorophenyl) methanol of Formula (5); and (c) carrying out a cyclisation reaction on the 4-substituted-2 hydroxymethylphenyl- 1-(4-fluorophenyl) methanol of Formula (5) following the reduction reaction, to form said intermediate of Formula (2); wherein R represents Br or CN.

Anti-depressive substituted 1-dimethylaminopropyl-1-phenyl phthalans

The present invention relates to phthalans of the following general formula: STR1 wherein R1 and R2 each represents halogen, a trifluoromethyl group, a cyano group or R--CO-- wherein R is an alkyl-radical with from 1-4 C-atoms inclusive, as well as acid addition salts thereof with pharmaceutically acceptable acids.