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1-(2-Aminocarbonylbenzofuran-5-yl)piperazine
Cas No: 183288-46-2
USD $ 3.0-3.0 / Kilogram
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Dayang Chem (Hangzhou) Co.,Ltd.
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High quality 1-(2-Aminocarbonylbenzofuran-5-yl)piperazine supplier in China
Cas No: 183288-46-2
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Simagchem Corporation
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Large Stock 99.0% 5-(1-Piperazinyl)benzofuran-2-carboxamide 183288-46-2 Producer
Cas No: 183288-46-2
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Xi'an Xszo Chem Co., Ltd.
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1-(2-Aminocarbonylbenzofuran-5-yl)piperazine
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Henan Allgreen Chemical Co.,Ltd
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Factory Supply 1-(2-Aminocarbonylbenzofuran-5-yl)piperazine
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Ality Chemical Corporation
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5-(1-Piperazinyl)benzofuran-2-carboxamide
Cas No: 183288-46-2
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Enke Pharma-tech Co.,Ltd. （Cangzhou, China ）
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5-(Piperazine-1-yl) benzofuran-2-carboxamide(183288-46-2)
Cas No: 183288-46-2
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Shanghai SE Pharm Co., Ltd
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1-(2-Aminocarbonylbenzofuran-5-yl)-piperazine
Cas No: 183288-46-2
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Chemwill Asia Co., Ltd.
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5-(1-Piperazinyl)benzofuran-2-carboxamide
Cas No: 183288-46-2
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Jinan Finer Chemical Co., Ltd
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5-(1-Piperazinyl)benzofuran-2-carboxamide
Cas No: 183288-46-2
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LIDE PHARMACEUTICALS LIMITED
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183288-46-2 Usage

Chemical Properties

Off-white Solid

Uses

Intermediate in the synthesis of Vilazodone (V265000).

Check Digit Verification of cas no

The CAS Registry Mumber 183288-46-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,3,2,8 and 8 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 183288-46:
(8*1)+(7*8)+(6*3)+(5*2)+(4*8)+(3*8)+(2*4)+(1*6)=162
162 % 10 = 2
So 183288-46-2 is a valid CAS Registry Number.

183288-46-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name	5-piperazin-1-yl-1-benzofuran-2-carboxamide

1.2 Other means of identification

Product number	-
Other names	5-(piperazin-1-yl)-1-benzofuran-2-carboxamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses	For industry use only.
Uses advised against	no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number	-
Service hours	Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:183288-46-2 SDS

183288-46-2Synthetic 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

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

: 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;

183288-46-2Upstream product

183288-46-2Downstream Products

183288-46-2Relevant articles and documents

Amidation and N-boc deprotection process improvement for the preparation of 5-(1-Piperazinyl)benzofuran-2-carboxamide, a key intermediate of vilazodone

Das, Prasenjit,Srivastava, Bindu,Joseph, Sony,Nizar, Hashim,Prasad, Mohan

, p. 665 - 667 (2014)

An improved process for the preparation of 5-(1-piperazinyl)benzofuran-2- carboxamide, a key intermediate used in the synthesis of antidepressant drug vilazodone is reported.

Preparation method of vilazodone hydrochloride

-

Paragraph 0063-0068; 0090-0092; 0093-0097, (2019/02/04)

The invention discloses a preparation method of vilazodone hydrochloride. The preparation method comprises the following steps: (1) in the presence of ammonium hydroxide or ammonium hydroxide and N-methylpyrrolidone, enabling 5-(1-piperazinyl)-benzofuran-2-ethyl formate hydrochloride to be subjected to ammonolysis reaction to obtain 5-(1-piperazinyl)-benzofuran-2-formamide; (2) in the presence ofalkali, enabling the 5-(1-piperazinyl)-benzofuran-2-formamide and 3-(4-chlorobutyl) indole-5-formonitrile to be subjected to nucleophilic substitution reaction to obtain a crude product of vilazodone,wherein the alkali is mixed alkali of sodium iodide, N,N-diisopropylethylamine and triethylamine or 1,8-diazabicycloundec-7-ene; (3) refining the crude product of vilazodone to obtain a refined product of vilazodone; and (4) enabling the refined product of vilazodone to be subjected to salt-forming reaction to obtain the vilazodone hydrochloride. By virtue of the ammonolysis reaction and the nucleophilic substitution reaction, the yield is higher, and the purity is higher; and the yield of the vilazodone hydrochloride is increased.

Preparation method of substituted benzobfuran-2-formamide

-

Paragraph 0047; 0048; 0049, (2016/10/08)

The invention belongs to the technical field of medicine, and discloses a preparation method of substituted benzobfuran-2-formamide (please see the formula in the specification). A compound shown in the formula (2) is obtained by removing the protecting group of a compound (3), and then 5-(1-piperazinyl)-benzofuran-2-formamide (1) is obtained through ammonolysis. The method overcomes the defects of an existing preparation method, operation is easy, use of expensive catalysts is avoided, intermediates can be conveniently separated, and cost is low.

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183288-46-2

183288-46-2

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183288-46-2Synthetic route

183288-46-2Upstream product

183288-46-2Downstream Products

183288-46-2Relevant articles and documents

Amidation and N-boc deprotection process improvement for the preparation of 5-(1-Piperazinyl)benzofuran-2-carboxamide, a key intermediate of vilazodone

Das, Prasenjit,Srivastava, Bindu,Joseph, Sony,Nizar, Hashim,Prasad, Mohan

, p. 665 - 667 (2014)

Preparation method of vilazodone hydrochloride

-

Paragraph 0063-0068; 0090-0092; 0093-0097, (2019/02/04)

Preparation method of substituted benzobfuran-2-formamide

-

Paragraph 0047; 0048; 0049, (2016/10/08)