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163521-11-7

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Basic Information
CAS No.: 163521-11-7
Name: 2-Benzofurancarboxylic acid, 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-, ethyl ester
Article Data: 5
Molecular Structure:
Molecular Structure of 163521-11-7 (2-Benzofurancarboxylic acid, 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-, ethyl ester)
Formula: C28H30N4O3
Molecular Weight: 470.571
Synonyms: 5-[4-[4-(5-Cyano-1H-indol-3-yl)butyl]-1-piperazi;
Density: 1.29
Boiling Point: 687.8±55.0 °C(Predicted)
PSA: 85.50000
LogP: 5.11028
Related products
Synthetic route
143612-79-7

3-(4-chlorobutyl)-5-cyanoindole

5-(1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester hydrochloride

163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile32%
With potassium carbonate; triethylamine In acetonitrile for 12h; Heating;
15861-24-2

1H-indole-5-carbonitrile

163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / isobutyl-AlCl2 / CH2Cl2 / 15 - 30 °C
2: 26 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene / 2 h
3: K2CO3; Et3N / acetonitrile / 12 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: isobutylaluminum dichloride / dichloromethane
2: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran
3: potassium carbonate / acetonitrile
View Scheme
69604-00-8

ethyl 5-nitrobenzo[d]furan-2-carboxylate

163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / H2 / Raney Ni / methanol / 27 h / 28 °C
2: 27 percent / K2CO3 / butan-1-ol / 48 h / Heating
3: K2CO3; Et3N / acetonitrile / 12 h / Heating
View Scheme
174775-48-5

ethyl 5-amino-1-benzofuran-2-carboxylate

163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 27 percent / K2CO3 / butan-1-ol / 48 h / Heating
2: K2CO3; Et3N / acetonitrile / 12 h / Heating
View Scheme
276863-95-7

3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 26 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene / 2 h
2: K2CO3; Et3N / acetonitrile / 12 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran
2: potassium carbonate / acetonitrile
View Scheme
143612-79-7

3-(4-chlorobutyl)-5-cyanoindole

5-(piperazin-1-yl)benzofuran-2-carboxylic acid ethyl ester

163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate; potassium iodide In acetonitrile at 20 - 82℃; for 24h; Reagent/catalyst;
Stage #1: 3-(4-chlorobutyl)-5-cyanoindole With copper(l) iodide In diethyl ether for 3.5h; Inert atmosphere; Reflux;
Stage #2: 5-(piperazin-1-yl)benzofuran-2-carboxylic acid ethyl ester With sodium methylate In diethyl ether at 90℃; for 5.5h; Concentration; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;		8.9 g
92886-57-2

1,1-dimethoxy-6-chlorohexane

163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: methanol; water / 1 h / 72 °C / Inert atmosphere
2.1: copper(l) iodide / diethyl ether / 3.5 h / Inert atmosphere; Reflux
2.2: 5.5 h / 90 °C / Inert atmosphere
View Scheme
56621-48-8

1-(4-hydroxyphenyl)piperazine

163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine; magnesium chloride / toluene / 7 h / Inert atmosphere; Reflux
2.1: sodium iodide; potassium carbonate / N,N-dimethyl-formamide / 5 h / Reflux
3.1: copper(l) iodide / diethyl ether / 3.5 h / Inert atmosphere; Reflux
3.2: 5.5 h / 90 °C / Inert atmosphere
View Scheme
163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

5-(4-(3-(5-cyano-1H-indol-3-yl)butyl)piperazin-1-yl)-benzofuran-2-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol80%
163521-11-7

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

163521-12-8

vilazodone

Conditions
ConditionsYield
With potassium hydroxide In methanol72%
Multi-step reaction with 2 steps
1: KOH / methanol / 3 h / Heating
2: 72 percent / 1-methyl-2-chloropyridinium iodide; Et2NiPr; NH3(g) / 1-methyl-pyrrolidin-2-one
View Scheme
With ammonium hydroxide In water; acetonitrile at 0 - 20℃; for 98h; Time; Reagent/catalyst; Temperature;
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Vilazodone ethyl ester dihydrochloride is a precursor to Vilazodone, a selective serotonin reuptake inhibitor and serotonin 1A receptor agonist that is used to treat patients with major depressive disorder.