1-(2-Aminocarbonylbenzofuran-5-yl)piperazine supplier

Name
5-(1-Piperazinyl)benzofuran-2-carboxamide
EINECS 1592732-453-0
CAS No. 183288-46-2
Article Data13
CAS DataBase
Density 1.269 g/cm³
Solubility
Melting Point
Formula C₁₃H₁₅N₃O₂
Boiling Point 505.319 °C at 760 mmHg
Molecular Weight 245.281
Flash Point 259.408 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5-(1-Piperazinyl)benzofuran-2-carboxamide;5-Piperazin-1-yl-1-benzofuran-2-carboxamide;
PSA 72.49000
LogP 2.21930

Synthetic route

: 5-(4-acetylpiperazin-1-yl)benzofuran-2-carboxylic acid ethyl ester hydrochloride

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

Conditions

Conditions	Yield
With ammonium hydroxide at 20℃; for 10h;	97%

: 110-85-0
piperazine

: 5-fluorobenzofuran-2-carboxamide

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

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 120℃; for 6h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;	93.9%

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

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

Conditions

Conditions	Yield
With ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 40 - 50℃; for 21h; Large scale;	80%

: 5-(4-acetylpiperazin-1-yl)benzofuran-2-carboxamide

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

Conditions

Conditions	Yield
Stage #1: 5-(4-acetylpiperazin-1-yl)benzofuran-2-carboxamide With hydrogenchloride In ethanol for 8h; Reflux; Stage #2: With ammonium hydroxide In ethanol at 20℃; for 1h;	78%

: 183288-44-0
tert-butyl 4-(2-carbamoyl-1-benzofuran-5-yl)piperazine-1-carboxylate

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

Conditions

Conditions	Yield
With hydrogenchloride In water at 35 - 50℃; for 1h; Large scale;	77.86%
In methanol hydrochloride

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

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

Conditions

Conditions	Yield
With ammonia In methanol at 25 - 30℃;	73.1%

: 110-85-0
piperazine

: 35351-20-3
5-chlorobenzofuran-2-carboxamide

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

Conditions

Conditions	Yield
With copper dichloride In dimethyl sulfoxide at 150℃; Reagent/catalyst; Solvent;	72%

: 110-85-0
piperazine

: 35351-21-4
5-bromo-2-carboxamidobenzo[b]furan

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

Conditions

Conditions	Yield
With copper(II) cyanide In N,N-dimethyl-formamide at 150℃; Reagent/catalyst; Solvent;	70%

: 110-85-0
piperazine

t-OBu: t-OBu

: 35351-21-4
5-bromo-2-carboxamidobenzo[b]furan

: 1-(N,N-dimethylamino)-1'-(dicyclohexylphosphino)biphenyl

: 7440-44-0
pyrographite

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

Conditions

Conditions	Yield
With hydrogenchloride; Pd(dba)2 In water; ethyl acetate; toluene

...Expand

P(t-Bu)3: P(t-Bu)3

t-OBu: t-OBu

: 35351-21-4
5-bromo-2-carboxamidobenzo[b]furan

: 57260-71-6
1-t-Butoxycarbonylpiperazine

A: 183288-44-0
tert-butyl 4-(2-carbamoyl-1-benzofuran-5-yl)piperazine-1-carboxylate

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

Conditions

Conditions	Yield
With hydrogenchloride; Pd(dba)2 In diethylene glycol dimethyl ether; water

...Expand

: 267644-49-5
5-nitro-1-benzofuran-2-carboxamide

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 2: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 3: hydrogen bromide; 4-hydroxy-benzoic acid / acetic acid / 50 °C View Scheme
Multi-step reaction with 2 steps 1.1: water; Pd/C; ammonium formate / methanol / 2 h / 30 - 45 °C 2.1: 2 h / 150 - 155 °C 2.2: 6 h / 150 - 155 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 2: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 3: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C View Scheme

: 5-amino-1-benzofuran-2-carboxamide

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 2: hydrogen bromide; 4-hydroxy-benzoic acid / acetic acid / 50 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 2: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C View Scheme

: 5-(4-tosylpiperazin-1-yl)benzofuran-2-carboxamide

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

Conditions

Conditions	Yield
With hydrogen bromide; 4-hydroxy-benzoic acid In acetic acid at 50℃;
With hydrogen bromide; acetic acid; 4-hydroxy-benzoic acid at 50℃; for 3h;

: 6280-80-4
2-Formylphenoxyacetic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: sulfuric acid; nitric acid / 5 - 35 °C 2.1: acetic anhydride / 0.25 h / 35 °C 2.2: 8 h / 125 °C 3.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 35 - 115 °C 3.2: 10 °C / pH 8 - 9 4.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 5.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 6.1: hydrogen bromide; 4-hydroxy-benzoic acid / acetic acid / 50 °C View Scheme
Multi-step reaction with 7 steps 1.1: sulfuric acid / water / 0.25 h / 5 - 35 °C 1.2: 2.25 h / 5 - 35 °C 2.1: acetic anhydride / 0.25 h / 35 °C 2.2: 8 h / 125 °C 3.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 0.5 h / 70 - 115 °C 4.1: ammonia / N,N-dimethyl-formamide / 10 °C / pH 8 - 9 5.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 6.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 7.1: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: sulfuric acid; nitric acid / 5 - 35 °C
2.1: acetic anhydride / 0.25 h / 35 °C
2.2: 8 h / 125 °C
3.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 35 - 115 °C
3.2: 10 °C / pH 8 - 9
4.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr
5.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C
6.1: hydrogen bromide; 4-hydroxy-benzoic acid / acetic acid / 50 °C
View Scheme

Multi-step reaction with 7 steps
1.1: sulfuric acid / water / 0.25 h / 5 - 35 °C
1.2: 2.25 h / 5 - 35 °C
2.1: acetic anhydride / 0.25 h / 35 °C
2.2: 8 h / 125 °C
3.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 0.5 h / 70 - 115 °C
4.1: ammonia / N,N-dimethyl-formamide / 10 °C / pH 8 - 9
5.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr
6.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C
7.1: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C
View Scheme

: 90-02-8
salicylaldehyde

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

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium hydroxide / water / 3 h / 30 - 100 °C 2.1: sulfuric acid; nitric acid / 5 - 35 °C 3.1: acetic anhydride / 0.25 h / 35 °C 3.2: 8 h / 125 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 35 - 115 °C 4.2: 10 °C / pH 8 - 9 5.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 6.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 7.1: hydrogen bromide; 4-hydroxy-benzoic acid / acetic acid / 50 °C View Scheme
Multi-step reaction with 8 steps 1.1: sodium hydroxide / water / 3 h / 30 - 100 °C 2.1: sulfuric acid / water / 0.25 h / 5 - 35 °C 2.2: 2.25 h / 5 - 35 °C 3.1: acetic anhydride / 0.25 h / 35 °C 3.2: 8 h / 125 °C 4.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 0.5 h / 70 - 115 °C 5.1: ammonia / N,N-dimethyl-formamide / 10 °C / pH 8 - 9 6.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 7.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 8.1: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: sodium hydroxide / water / 3 h / 30 - 100 °C
2.1: sulfuric acid; nitric acid / 5 - 35 °C
3.1: acetic anhydride / 0.25 h / 35 °C
3.2: 8 h / 125 °C
4.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 35 - 115 °C
4.2: 10 °C / pH 8 - 9
5.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr
6.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C
7.1: hydrogen bromide; 4-hydroxy-benzoic acid / acetic acid / 50 °C
View Scheme

Multi-step reaction with 8 steps
1.1: sodium hydroxide / water / 3 h / 30 - 100 °C
2.1: sulfuric acid / water / 0.25 h / 5 - 35 °C
2.2: 2.25 h / 5 - 35 °C
3.1: acetic anhydride / 0.25 h / 35 °C
3.2: 8 h / 125 °C
4.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 0.5 h / 70 - 115 °C
5.1: ammonia / N,N-dimethyl-formamide / 10 °C / pH 8 - 9
6.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr
7.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C
8.1: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C
View Scheme

: 6965-69-1
2-(2-formyl-4-nitrophenoxy)acetic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: acetic anhydride / 0.25 h / 35 °C 1.2: 8 h / 125 °C 2.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 35 - 115 °C 2.2: 10 °C / pH 8 - 9 3.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 4.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 5.1: hydrogen bromide; 4-hydroxy-benzoic acid / acetic acid / 50 °C View Scheme
Multi-step reaction with 6 steps 1.1: acetic anhydride / 0.25 h / 35 °C 1.2: 8 h / 125 °C 2.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 0.5 h / 70 - 115 °C 3.1: ammonia / N,N-dimethyl-formamide / 10 °C / pH 8 - 9 4.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 5.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 6.1: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: acetic anhydride / 0.25 h / 35 °C
1.2: 8 h / 125 °C
2.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 35 - 115 °C
2.2: 10 °C / pH 8 - 9
3.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr
4.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C
5.1: hydrogen bromide; 4-hydroxy-benzoic acid / acetic acid / 50 °C
View Scheme

Multi-step reaction with 6 steps
1.1: acetic anhydride / 0.25 h / 35 °C
1.2: 8 h / 125 °C
2.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 0.5 h / 70 - 115 °C
3.1: ammonia / N,N-dimethyl-formamide / 10 °C / pH 8 - 9
4.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr
5.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C
6.1: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C
View Scheme

: 10242-12-3
5-nitrobenzofuran-2-carboxylic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 35 - 115 °C 1.2: 10 °C / pH 8 - 9 2.1: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 3.1: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 4.1: hydrogen bromide; 4-hydroxy-benzoic acid / acetic acid / 50 °C View Scheme
Multi-step reaction with 5 steps 1: thionyl chloride / toluene; N,N-dimethyl-formamide / 0.5 h / 70 - 115 °C 2: ammonia / N,N-dimethyl-formamide / 10 °C / pH 8 - 9 3: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 4: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 5: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C View Scheme

: 1646-29-3
5-aminobenzofuran-2-carboxylic acid methyl ester

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tributyl-amine / 43 h / 73 - 77 °C 2: sulfuric acid / 0.25 h / 25 - 102 °C 3: ammonia / methanol / 25 - 30 °C View Scheme

: methyl 5-[4-(benzenesulfonyl)-1-piperazinyl]benzofuran-2-carboxylate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 0.25 h / 25 - 102 °C 2: ammonia / methanol / 25 - 30 °C View Scheme

: 1602487-82-0
5-(4-formylpiperazin-1-yl)-1-benzofuran-2-carboxamide

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

Conditions

Conditions	Yield
With hydrogenchloride In water at 45 - 50℃; for 1h;	24 g

: 5-amino-1-benzofuran-2-carboxamide

: 334-22-5
N,N-bis(chloro-2-ethyl)amine

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

Conditions

Conditions	Yield
Stage #1: 5-amino-1-benzofuran-2-carboxamide; N,N-bis(chloro-2-ethyl)amine at 150 - 155℃; for 2h; Stage #2: With tributyl-amine In 1-methyl-pyrrolidin-2-one at 150 - 155℃; for 6h;	5.6 g

: 69604-00-8
ethyl 5-nitrobenzo[d]furan-2-carboxylate

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: formamide; sodium methylate / 1-methyl-pyrrolidin-2-one / 2 h / 20 - 25 °C 2.1: water; Pd/C; ammonium formate / methanol / 2 h / 30 - 45 °C 3.1: 2 h / 150 - 155 °C 3.2: 6 h / 150 - 155 °C View Scheme

: ethyl 5-(4-tert-butoxycarbonyl-1-piperazinyl)benzofuran-2-carboxylate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: formamide; sodium methylate / methanol / 1 h / 20 - 30 °C / Large scale 2: hydrogenchloride / water / 1 h / 35 - 50 °C / Large scale View Scheme

: 90036-16-1
5-nitrobenzofuran-2-carbonyl chloride

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: ammonia / N,N-dimethyl-formamide / 10 °C / pH 8 - 9 2: hydrogen / methanol / 14 h / 35 - 60 °C / 4500.45 Torr 3: N-ethyl-N,N-diisopropylamine / 10 h / 120 °C 4: 4-hydroxy-benzoic acid; hydrogen bromide; acetic acid / 3 h / 50 °C View Scheme

: 347-54-6
5-fluoro-2-hydroxybenzaldehyde

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium methylate / diethyl ether / 0.2 h / 20 °C / Inert atmosphere 1.2: 8 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / dimethyl sulfoxide / 6 h / 120 °C / Inert atmosphere View Scheme

: 1761-61-1
5-bromosalicyclaldehyde

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / ethyl acetate / 6 h / Reflux 1.2: 3 h / 80 °C 2.1: N,N-dimethyl-formamide / 6 h / 140 °C 3.1: thionyl chloride / 1,2-dichloro-ethane / 4 h / 60 °C 4.1: ammonia / tetrahydrofuran / 0.5 h / 25 °C / 2250.23 Torr View Scheme

: 10242-11-2
5-bromobenzo[b]furan-2-carboxylic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 6 h / 140 °C 2: thionyl chloride / 1,2-dichloro-ethane / 4 h / 60 °C 3: ammonia / tetrahydrofuran / 0.5 h / 25 °C / 2250.23 Torr View Scheme

: 5-(piperazin-1-yl)benzofuran-2-carboxylic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 1,2-dichloro-ethane / 4 h / 60 °C 2: ammonia / tetrahydrofuran / 0.5 h / 25 °C / 2250.23 Torr View Scheme

: C13H13ClN2O2

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

Conditions

Conditions	Yield
With ammonia In tetrahydrofuran at 25℃; under 2250.23 Torr; for 0.5h;	196 g

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

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

: 163521-12-8
vilazodone

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
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; Temperature; Solvent; Reagent/catalyst;	95.7%

: 914927-40-5
3-(4-hydroxybutyl)-1H-indole-5-carbonitrile

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

: 163521-12-8
vilazodone

Conditions

Conditions	Yield
With trifluoroacetic acid at 60℃; for 12h; Temperature;	91.2%

: 3-(4-bromobutyl)-1-(p-toluenesulfonyl)-1H-indole-5-carbonitrile

: 183288-46-2
5-(1-piperazinyl)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

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 5h;	86%

: 276863-95-7
3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

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

: vilazodone N-oxide

Conditions

Conditions	Yield
With triethylamine; potassium iodide In N,N-dimethyl-formamide at 20 - 90℃; for 49h; Inert atmosphere;	85%
With tributyl-amine In 1-methyl-pyrrolidin-2-one at 25 - 130℃; for 24h;	7%

: 3-(4-bromobutyl)-1-(phenylsulfonyl)-1H-indole-5-carbonitrile

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

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

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 6h; Reagent/catalyst; Solvent;	84%

: 3-(4-bromobutyl)-1-(naphthalene-2-yl-sulfonyl)-1H-indole-5-carbonitrile

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

: 5-[4-[4-[5-cyano-1-(naphthalene-2-yl-sulfonyl)-1H-indol-3-yl]butyl]piperazin-1-yl]-2-benzofurancarboxamide

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 5h;	82%

: 3-(4-bromobutyl)-1-(naphthalen-1-yl-sulfonyl)-1H-indole-5-carbonitrile

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

: 5-[4-[4-[5-cyano-1-(naphthalen-1-yl-sulfonyl)-1H-indol-3-yl]butyl]piperazin-1-yl]-2-benzofurancarboxamide

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 5h;	79%

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

: 714950-87-5
methanesulfonic acid 5-cyano-3-(4-methanesulfonyloxy-butyl)-1H-indol-6-yl ester

: 714950-88-6
methanesulfonic acid 3-{4-[4-(2-carbamoyl-benzofuran-5-yl)-piperazin-1-yl]-butyl}-5-cyano-1H-indol-6-yl ester

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one at 120℃;	77%

: 3-(4-chlorobutyl)-1-(naphthalen-1-yl-sulfonyl)-1H-indole-5-carbonitrile

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

: 5-[4-[4-[5-cyano-1-(naphthalen-1-yl-sulfonyl)-1H-indol-3-yl]butyl]piperazin-1-yl]-2-benzofurancarboxamide

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 5h;	76%

: 913730-89-9
3-(4-oxobutyl)-1H-indole-5-carbonitrile

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

: 163521-12-8
vilazodone

Conditions

Conditions	Yield
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%

: 913730-89-9
3-(4-oxobutyl)-1H-indole-5-carbonitrile

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

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

Conditions

Conditions	Yield
Stage #1: 5-(1-piperazinyl)benzofuran-2-carboxamide With methanol; sodium cyanoborohydride at 20℃; Stage #2: 3-(4-oxobutyl)-1H-indole-5-carbonitrile at 20℃; for 18.25h;	75.21%

: 3-(4-chlorobutyl)-1-(naphthalen-2-yl-sulfonyl)-1H-indole-5-carbonitrile

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

: 5-[4-[4-[5-cyano-1-(naphthalene-2-yl-sulfonyl)-1H-indol-3-yl]butyl]piperazin-1-yl]-2-benzofurancarboxamide

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 5.5h;	72%

: 816429-22-8
C14H15ClN2

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

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

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; triethylamine at 20 - 120℃; for 14h;

: 816438-46-7
3-(4-chloro-butyl)-2,3-dihydro-1H-indole-5-carbonitrile

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

: 5-{4-[4-(5-cyano-2,3-dihydro-1H-indol-3-yl)-butyl]-piperazin-1-yl}-benzofuran-2-carboxamide hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-(4-chloro-butyl)-2,3-dihydro-1H-indole-5-carbonitrile; 5-(1-piperazinyl)benzofuran-2-carboxamide With 1-methyl-pyrrolidin-2-one at 125℃; for 24h; Stage #2: With sodium hydroxide In water at 0℃; pH=10; Stage #3: With hydrogenchloride In water; acetone pH=3;

: 913730-89-9
3-(4-oxobutyl)-1H-indole-5-carbonitrile

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

: vilazodone hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-(4-oxobutyl)-1H-indole-5-carbonitrile; 5-(1-piperazinyl)benzofuran-2-carboxamide With sodium cyanoborohydride In methanol at 10 - 20℃; for 24.25h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; Product distribution / selectivity;

: 872-50-4
1-methyl-pyrrolidin-2-one

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

: 5-{4-[4-(5-cyano-2,3-dihydro-1H-indol-3-yl)butyl]piperazin-1-yl}benzofuran-2-carboxamide

Conditions

Conditions	Yield
With sodium hydroxide In methanol; ice-water; water; ethyl acetate

: 113964-33-3
(6-chloro-1-hexyn-1-yl)trimethylsilane

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

: 1187322-52-6
5-[4-(6-trimethylsilanyl-hex-5-ynyl)-piperazin-1-yl]-benzofuran-2-carboxylic acid amide

Conditions

Conditions	Yield
With triethylamine In acetonitrile for 72h; Heating;

1-(2-Aminocarbonylbenzofuran-5-yl)piperazine Specification

The 2-Benzofurancarboxamide, 5-(1-piperazinyl)-, with the CAS registry number 183288-46-2, is also known as 5-(1-Piperazinyl)benzofuran-2-carboxamide. This chemical's molecular formula is C₁₃H₁₅N₃O₂ and molecular weight is 245.28. What's more, its systematic name is 5-piperazin-1-yl-1-benzofuran-2-carboxamide.

Physical properties of 2-Benzofurancarboxamide, 5-(1-piperazinyl)- are: (1)ACD/LogP: -0.13; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2; (4)ACD/LogD (pH 7.4): -1; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 2; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 71.5 Å²; (13)Index of Refraction: 1.631; (14)Molar Refractivity: 68.878 cm³; (15)Molar Volume: 193.346 cm³; (16)Polarizability: 27.305×10^-24cm³; (17)Surface Tension: 53.254 dyne/cm; (18)Density: 1.269 g/cm³; (19)Flash Point: 259.408 °C; (20)Enthalpy of Vaporization: 77.497 kJ/mol; (21)Boiling Point: 505.319 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c2oc1ccc(cc1c2)N3CCNCC3)N
(2)Std. InChI: InChI=1S/C13H15N3O2/c14-13(17)12-8-9-7-10(1-2-11(9)18-12)16-5-3-15-4-6-16/h1-2,7-8,15H,3-6H2,(H2,14,17)
(3)Std. InChIKey: LLRGOAFFRRUFBM-UHFFFAOYSA-N

Product Name

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

Synthetic route

1-(2-Aminocarbonylbenzofuran-5-yl)piperazine Specification

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