3245-49-6

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-(3-Bromopropoxy)-3-methoxyphenyl)ethanone is used as a reagent for the preparation of psychotropic agents, specifically for the synthesis of iloperidone. Iloperidone is an atypical antipsychotic drug used in the treatment of schizophrenia and other mental disorders. 1-(4-(3-bromopropoxy)3-methoxyphenyl)ethanone plays a crucial role in the chemical synthesis process, enabling the production of effective and safe psychotropic medications.

Upstream product

• 109-70-6 1.3-chlorobromopropane 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 109-64-8 1,3-dibromo-propane 

Downstream Products

• 47553-92-4 N-<2-(2-Methoxy-phenoxy)-aethyl>-3-<4-acetyl-2-methoxy-phenoxy>-propylamin 
• 1446339-55-4 (S)-3-{1-[3-(4-acetyl-2-methoxyphenoxy)propyl]piperidin-2-yl}pyridine oxalate 
• 133454-47-4 iloperidone 
• 1184831-17-1 1-[5-methoxy-4-(3-bromo-propoxy)-2-nitro-phenyl]-ethanone 
• 1160707-44-7 1-[4-(3-chloropropoxy)-5-methoxy-2-nitrophenyl]ethan-1-one 
• 152808-10-1 1-[4-[3-[4-(6-fluorobenzo[b]thiophen-3-yl)-1-piperazinyl]propoxy]-3-methoxyphenyl]ethanone 
• 198133-52-7 1-[4-[3-(7-fluoro-1,4-dihydrospiro[cyclopent[b]indole-3(2H),4'-piperidine]-1'-yl)propoxy]-3-methoxyphenyl]ethanone 

Relevant academic research and scientific papers

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

Improved and efficient process for the production of highly pure iloperidone: A psychotropic agent

The present work describes an improved and highly efficient process for the synthesis of iloperidone (1), an antipsychotic agent, which is free from potential impurities. The synthesis comprises N-alkylation of 1-(4-(3-chloropropoxy)-3-methoxyphenyl)ethanone (4) with 6-fluoro-3-piperidin-4- yl-1,2-benzisoxazole hydrochloride (5) in a mixture of water and heptane as solvent and sodium hydroxide as a base in the presence of tetrabutylammonium bromide as a phase transfer catalyst to yield iloperidone (1) with a yield of around 95% and a purity of 99.80% by HPLC. The present work also describes the optimization details performed to achieve the process attributes responsible for high yield and purity.

Synthesis of N-aryloxyalkylanabasine derivatives

N-Aryloxyalkylanabasine derivatives were prepared via the reaction of anabasine hydrochloride with various aryloxyhaloalkanes in the presence of potash in DMF. The reaction occurred with retention of the chiral center C-(2) of the piperidine group. Side products of bis(aryloxy)ethanes were characterized.

Isolation and characterization of process related substances of an antipsychotic drug: Iloperidone

Seven unknown recurring impurities were isolated during the synthesis of Iloperidone process. All six impurities were subsequently synthesized and characterized by FTIR, MS and NMR spectral data. The structures of impurities were confirmed as 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (4), 1-[4-(3-hydroxypropoxy)-3-methoxy phenyl]ethanone (7), 1-[4-(3-bromopropoxy)-3- methoxyphenyl] ethanone (9), 1,1'-[4,4'-(propane-1,3-diylbis(oxy))bis(3-methoxy- 4,1-phenylene)]diethanone (10), 1-[3-(4-acetyl-2-methoxyphenoxy)-propyl]-4-(6- fluorobenzo[d]isoxazol-3-yl)piperidine-1-oxide (11) and in final other two impurities 1-(4-hydroxy-3-methoxyphenyl)-ethanone (2) and 6-fluoro-3-(piperidin- 4-yl)benzo[d]isoxazole (5). The present work describes the formation, synthesis and characterization of these impurities.

PROCESS FOR THE PREPARATION OF ILOPERIDONE

The present invention relates to a novel process for the preparation of iloperidone (I) that comprises reaction of 1-[4-(3-halopropoxy)-3-methoxyphenyl] ethanone (IIIa / IIIb) with 6- fluoro-3-(piperidine-4-yl)-1,2-benzisoxazole hydrochloride (II) under pressure in an autoclave.