Product Name

  • Name

    VILAZODONE

  • EINECS 1308068-626-2
  • CAS No. 163521-12-8
  • Article Data30
  • CAS DataBase
  • Density 1.343 g/cm3
  • Solubility
  • Melting Point 203-205 °C
  • Formula C26H27N5O2
  • Boiling Point 745.076 °C at 760 mmHg
  • Molecular Weight 441.533
  • Flash Point 404.408 °C
  • Transport Information
  • Appearance Light yellow solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 163521-12-8 (VILAZODONE)
  • Hazard Symbols
  • Synonyms 5-[4-[4-(5-Cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide;AC1OCFA2;CID6918314;5-[4-[4-(5-Ccyano-1H-indol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxamide;UNII-S239O2OOV3;
  • PSA 102.29000
  • LogP 5.53478

Synthetic route

methyl 5-{4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-benzofuran-2-carboxylate
1236722-93-2

methyl 5-{4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-benzofuran-2-carboxylate

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
With ammonia In methanol at 25 - 30℃; Concentration; Pressure; Time;98.5%
With ammonia In methanol at 20℃; for 20h;Ca. 3 g
With ammonia In methanol at 25 - 30℃;11g
3-(4-chlorobutyl)-5-cyanoindole
143612-79-7

3-(4-chlorobutyl)-5-cyanoindole

5-(1-piperazinyl)benzofuran-2-carboxamide
183288-46-2

5-(1-piperazinyl)benzofuran-2-carboxamide

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: 3-(4-chlorobutyl)-5-cyanoindole With sodium iodide In N,N-dimethyl-formamide at 25 - 30℃; for 0.25h;
Stage #2: 5-(1-piperazinyl)benzofuran-2-carboxamide With tetrabutylammomium bromide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 110 - 115℃; for 1.25h; Reagent/catalyst; Temperature; Time; Solvent;		95.7%
With sodium carbonate In water at 90 - 100℃;94%
Stage #1: 5-(1-piperazinyl)benzofuran-2-carboxamide With hydrogenchloride In water at 20 - 35℃; pH=6.5 - 7;
Stage #2: 3-(4-chlorobutyl)-5-cyanoindole With sodium carbonate In water; isopropyl alcohol at 75 - 85℃; for 12h; Reagent/catalyst; pH-value;		94%
5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzofurancarboxylic acid ethyl ester hydrochloride
1422956-25-9

5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzofurancarboxylic acid ethyl ester hydrochloride

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 50℃; for 22h; Reagent/catalyst; Time; Temperature; Autoclave;93%
Stage #1: 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzofurancarboxylic acid ethyl ester hydrochloride With potassium carbonate In dichloromethane
Stage #2: With sodium methylate; formamide In tetrahydrofuran at 20 - 30℃;		90%
With ammonia In dimethyl sulfoxide at 20 - 35℃;81.6%
With ammonium hydroxide In 1-methyl-pyrrolidin-2-one40.5 g
3-(4-hydroxybutyl)-1H-indole-5-carbonitrile
914927-40-5

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

5-(1-piperazinyl)benzofuran-2-carboxamide
183288-46-2

5-(1-piperazinyl)benzofuran-2-carboxamide

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
With trifluoroacetic acid at 60℃; for 12h; Temperature;91.2%
ClH*C33H38N4O5

ClH*C33H38N4O5

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: ClH*C33H38N4O5 With potassium carbonate In dichloromethane
Stage #2: With sodium methylate; formamide In tetrahydrofuran at 20 - 30℃; for 8h;		90%
ClH*C34H40N4O5

ClH*C34H40N4O5

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: ClH*C34H40N4O5 With potassium carbonate In dichloromethane
Stage #2: With sodium methylate; formamide In tetrahydrofuran at 20 - 30℃;		90%
n-butyl 5-(4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxylate hydrochloride

n-butyl 5-(4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxylate hydrochloride

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: n-butyl 5-(4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxylate hydrochloride With potassium carbonate In dichloromethane
Stage #2: With sodium methylate; formamide In tetrahydrofuran at 20 - 30℃; Reagent/catalyst; Solvent; Temperature;		85%
5-[4-[4-[5-cyano-1-(p-toluenesulfonyl)-1H-indol-3-yl]butyl]piperazin-1-yl]benzofuran-2-carboxamide
1415760-77-8

5-[4-[4-[5-cyano-1-(p-toluenesulfonyl)-1H-indol-3-yl]butyl]piperazin-1-yl]benzofuran-2-carboxamide

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20 - 65℃; for 2h;84.1%
With sodium hydroxide In methanol at 60 - 65℃; for 2h;81%
With potassium carbonate In methanol; water for 2h; Inert atmosphere; Reflux;
5-piperazin-1-ylbenzofuran-2-carboxamide hydrochloride

5-piperazin-1-ylbenzofuran-2-carboxamide hydrochloride

3-(4-chlorobutyl)-5-cyanoindole
143612-79-7

3-(4-chlorobutyl)-5-cyanoindole

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
With potassium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 95 - 105℃; for 20h;83%
vilazodone N-oxide

vilazodone N-oxide

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
With sodium tetrahydroborate; trifluoroacetic acid In dichloromethane at 10 - 45℃; for 16h;82.5%
ethyl 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylate hydrochloride

ethyl 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylate hydrochloride

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
With ammonia In dimethyl sulfoxide at 20 - 35℃; under 3750.38 - 4500.45 Torr;81.6%
5-(4-(3-(5-cyano-1H-indol-3-yl)butyl)piperazin-1-yl)-benzofuran-2-carboxylic acid

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

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: 5-(4-(3-(5-cyano-1H-indol-3-yl)butyl)piperazin-1-yl)-benzofuran-2-carboxylic acid With 1,1'-carbonyldiimidazole In methanol at 20℃; for 1h; Reflux; Large scale;
Stage #2: With ammonia In N,N-dimethyl-formamide for 0.5h; Reagent/catalyst; Large scale;		81%
3-(4-oxobutyl)-1H-indole-5-carbonitrile
913730-89-9

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

5-(1-piperazinyl)benzofuran-2-carboxamide
183288-46-2

5-(1-piperazinyl)benzofuran-2-carboxamide

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: 5-(1-piperazinyl)benzofuran-2-carboxamide With sodium cyanoborohydride In methanol at 20℃;
Stage #2: 3-(4-oxobutyl)-1H-indole-5-carbonitrile In methanol at 20℃; for 18h;		75.21%
5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylic acid
163521-19-5

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

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
With N,N-diethyl-N-isopropylamine; 2-chloro-1-methyl-pyridinium iodide; ammonia In 1-methyl-pyrrolidin-2-one72%
5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)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

vilazodone
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;
n-propyl 5-(piperazin-1-yl)benzofuran-2-carboxylate

n-propyl 5-(piperazin-1-yl)benzofuran-2-carboxylate

3-(4-chlorobutyl)-5-cyanoindole
143612-79-7

3-(4-chlorobutyl)-5-cyanoindole

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: n-propyl 5-(piperazin-1-yl)benzofuran-2-carboxylate; 3-(4-chlorobutyl)-5-cyanoindole With tetrabutylammomium bromide; potassium carbonate; potassium iodide In acetonitrile Reflux;
Stage #2: With ammonium hydroxide In acetonitrile at 25 - 30℃; for 72h;		72%
isopropyl 5-(piperazin-1-yl)benzofuran-2-carboxylate

isopropyl 5-(piperazin-1-yl)benzofuran-2-carboxylate

3-(4-chlorobutyl)-5-cyanoindole
143612-79-7

3-(4-chlorobutyl)-5-cyanoindole

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: isopropyl 5-(piperazin-1-yl)benzofuran-2-carboxylate; 3-(4-chlorobutyl)-5-cyanoindole With tetrabutylammomium bromide; potassium carbonate; potassium iodide In acetonitrile Reflux;
Stage #2: With ammonium hydroxide In acetonitrile at 25 - 30℃; for 72h;		70%
n-butyl 5-(piperazin-1-yl)benzofuran-2-carboxylate

n-butyl 5-(piperazin-1-yl)benzofuran-2-carboxylate

3-(4-chlorobutyl)-5-cyanoindole
143612-79-7

3-(4-chlorobutyl)-5-cyanoindole

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: n-butyl 5-(piperazin-1-yl)benzofuran-2-carboxylate; 3-(4-chlorobutyl)-5-cyanoindole With tetrabutylammomium bromide; potassium carbonate; potassium iodide In acetonitrile Reflux;
Stage #2: With ammonium hydroxide In acetonitrile at 25 - 30℃; for 72h;		70%
methyl 5-(1-piperazinyl)-benzofuran-2-carboxylate

methyl 5-(1-piperazinyl)-benzofuran-2-carboxylate

3-(4-chlorobutyl)-5-cyanoindole
143612-79-7

3-(4-chlorobutyl)-5-cyanoindole

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Stage #1: methyl 5-(1-piperazinyl)-benzofuran-2-carboxylate; 3-(4-chlorobutyl)-5-cyanoindole With tetrabutylammomium bromide; potassium carbonate; potassium iodide In acetonitrile Reflux;
Stage #2: With ammonium hydroxide In acetonitrile at 25 - 30℃; for 72h;		65%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Multi-step reaction with 5 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
4: KOH / methanol / 3 h / Heating
5: 72 percent / 1-methyl-2-chloropyridinium iodide; Et2NiPr; NH3(g) / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 4 steps
1: isobutylaluminum dichloride / dichloromethane
2: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran
3: potassium carbonate / acetonitrile
4: potassium hydroxide / methanol
View Scheme
Multi-step reaction with 5 steps
1.1: isobutylaluminum dichloride / dichloromethane
2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran
3.1: potassium carbonate / acetonitrile
4.1: potassium hydroxide / methanol
5.1: 1,1'-carbonyldiimidazole / methanol / 1 h / 20 °C / Reflux; Large scale
5.2: 0.5 h / Large scale
View Scheme
ethyl 5-nitrobenzo[d]furan-2-carboxylate
69604-00-8

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

vilazodone
163521-12-8

vilazodone

Conditions
ConditionsYield
Multi-step reaction with 5 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
4: KOH / methanol / 3 h / Heating
5: 72 percent / 1-methyl-2-chloropyridinium iodide; Et2NiPr; NH3(g) / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 33 - 38 °C / 3000.3 - 3750.38 Torr
2.1: tetrabutylammomium bromide; potassium carbonate / o-xylene / 32 h / 135 - 140 °C
3.1: tetrabutylammomium bromide; triethylamine / 10 h / 85 - 90 °C
3.2: 50 - 55 °C / pH 2 / Reflux
4.1: ammonia / dimethyl sulfoxide / 20 - 35 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 33 - 38 °C / 3000.3 - 3750.38 Torr
2.1: tetrabutylammomium bromide; potassium carbonate / o-xylene / 32 h / 135 - 140 °C
3.1: tetrabutylammomium bromide; triethylamine / 10 h / 85 - 90 °C
3.2: 50 - 55 °C / pH 2 / Reflux
4.1: ammonia / dimethyl sulfoxide / 20 - 35 °C
View Scheme
vilazodone
163521-12-8

vilazodone

5-(4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxamide hydrochloride

5-(4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxamide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water; acetone at 55℃; for 0.5h; pH=1;99%
With hydrogenchloride In isopropyl alcohol at 80℃; Temperature;98.7%
Stage #1: vilazodone With pyrographite In isopropyl alcohol at 25 - 30℃; for 0.0833333h;
Stage #2: With isopropanolic hydrochloride In isopropyl alcohol at 20 - 45℃; for 2h; Temperature; Time; Solvent;		92%
vilazodone
163521-12-8

vilazodone

vilazodone hydrochloride

vilazodone hydrochloride

Conditions
ConditionsYield
Stage #1: vilazodone In isopropyl alcohol for 0.75h; Reflux;
Stage #2: With hydrogenchloride In isopropyl alcohol at 60 - 70℃;		98%
Stage #1: vilazodone With pyrographite In tetrahydrofuran
Stage #2: With hydrogenchloride In tetrahydrofuran		98.7%
With hydrogenchloride In tetrahydrofuran; water at 35 - 50℃; for 1h;95%
trifluoroacetic acid
76-05-1

trifluoroacetic acid

vilazodone
163521-12-8

vilazodone

5-(4-(4-(5-cyanoindol-3-yl)butyl)-1-piperazinyl)-2-benzofurancarboxamide trifluoroacetate

5-(4-(4-(5-cyanoindol-3-yl)butyl)-1-piperazinyl)-2-benzofurancarboxamide trifluoroacetate

Conditions
ConditionsYield
In ethyl acetate at 85℃; Solvent; Temperature;93.1%
vilazodone
163521-12-8

vilazodone

5-(4-(4-(5-cyanoindol-3-yl)butyl)-1-piperazinyl)-2-benzofurancarboxamide sulfate

5-(4-(4-(5-cyanoindol-3-yl)butyl)-1-piperazinyl)-2-benzofurancarboxamide sulfate

Conditions
ConditionsYield
With sulfuric acid In n-heptane at 95℃; Reagent/catalyst; Solvent;92.3%
2(13)CN(1-)*Zn(2+)

2(13)CN(1-)*Zn(2+)

vilazodone
163521-12-8

vilazodone

[13CN]-vilazodone

[13CN]-vilazodone

Conditions
ConditionsYield
With dmap; bis(1,5-cyclooctadiene)nickel(0); trimethylphosphane In toluene at 130℃; for 12h; Glovebox; Sealed tube;91%

Vilazodone Specification

The Vilazodone with CAS registry number of 163521-12-8 is also known as 2-Benzofurancarboxamide, 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-. The IUPAC name is 5-[4-[4-(5-Cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide. In addition, the formula is C26H27N5O2 and the molecular weight is 441.52. Besides, this chemical is an antidepressant developed for the treatment of major depressive disorder.

Physical properties about Vilazodone are: (1)ACD/LogP: 3.99 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 2.26 ; (4)ACD/LogD (pH 7.4): 3.76 ; (5)ACD/BCF (pH 5.5): 11.76; (6)ACD/BCF (pH 7.4): 371.61; (7)ACD/KOC (pH 5.5): 65.58; (8)ACD/KOC (pH 7.4): 2071.96; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 68.65Å2; (13)Index of Refraction: 1.711; (14)Molar Refractivity: 128.68 cm3; (15)Molar Volume: 328.7 cm3; (16)Surface Tension: 75.2 dyne/cm; (17)Density: 1.34 g/cm3; (18)Flash Point: 404.4 °C; (19)Enthalpy of Vaporization: 108.63 kJ/mol; (20)Boiling Point: 745.1 °C at 760 mmHg; (21)Vapour Pressure: 4.5E-22 mmHg at 25°C.

People can use the following data to convert to the molecule structure.
1.SMILES: N#Cc1ccc2c(c1)c(cn2)CCCCN5CCN(c4cc3c(oc(c3)C(=O)N)cc4)CC5
2.InChI: InChI=1/C26H27N5O2/c27-16-18-4-6-23-22(13-18)19(17-29-23)3-1-2-8-30-9-11-31(12-10-30)21-5-7-24-20(14-21)15-25(33-24)26(28)32/h4-7,13-15,17,29H,1-3,8-12H2,(H2,28,32) 
3.InChIKey: SGEGOXDYSFKCPT-UHFFFAOYAC
4.Std. InChI: InChI=1S/C26H27N5O2/c27-16-18-4-6-23-22(13-18)19(17-29-23)3-1-2-8-30-9-11-31(12-10-30)21-5-7-24-20(14-21)15-25(33-24)26(28)32/h4-7,13-15,17,29H,1-3,8-12H2,(H2,28,32).

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