Darifenacin supplier | CasNO.133099-04-4

Name
Darifenacin
EINECS
CAS No. 133099-04-4
Article Data10
CAS DataBase
Density 1.192 g/cm³
Solubility
Melting Point
Formula C₂₈H₃₀N₂O₂
Boiling Point 614.3 °C at 760 mmHg
Molecular Weight 426.558
Flash Point 325.3 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-Pyrrolidineacetamide,1-[2-(2,3-dihydro-5-benzofuranyl)ethyl]-a,a-diphenyl-, (S)-;(3S)-3-(2-Amino-2-oxo-1,1-diphenylethyl)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-1-pyrrolidine;(S)-(-)-3-(1-Carbamoyl-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine;(S)-1-[2-(2,3-Dihydro-5-benzofuranyl)ethyl]-a,a-diphenyl-3-pyrrolidineacetamide;(S)-3-(1-Carbamoyl-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine;UK 88525;3-Pyrrolidineacetamide,1-[2-(2,3-dihydro-5-benzofuranyl)ethyl]-a,a-diphenyl-, (3S)-;
PSA 55.56000
LogP 4.59570

Synthetic route

: (3S)-3-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidine

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In iso-butanol for 48h; Reflux;	80%

: 55745-68-1
(2,3-dihydrobenzo[b]furan-5-yl)methyl chloride

: potassium (S)-((3-(cyanodiphenylmethyl)pyrrolidin-1-yl)-methyl)trifluoroborate

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Stage #1: (2,3-dihydrobenzo[b]furan-5-yl)methyl chloride; potassium (S)-((3-(cyanodiphenylmethyl)pyrrolidin-1-yl)-methyl)trifluoroborate With potassium tert-butylate In tert-Amyl alcohol; water at 110℃; for 20h; Inert atmosphere; Stage #2: With tetrabutylammomium bromide; potassium hydroxide In tert-Amyl alcohol at 110℃; for 24h; Inert atmosphere;	46%

: 127264-14-6
2,3-dihydro-5-(2-bromoethyl)benzofuran

: 134002-25-8
2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 2h; Heating / reflux;	9%
With potassium phosphate In water; toluene at 20 - 90℃; for 3.5h; Product distribution / selectivity;
With potassium carbonate In water; toluene at 20 - 90℃; for 3.5h; Product distribution / selectivity;
With potassium phosphate In cyclohexane; water at 20 - 90℃; for 3.5h; Product distribution / selectivity;
With potassium hydroxide In acetonitrile at 40 - 50℃; for 18h; Product distribution / selectivity;

: 133033-99-5
(S)-2-{1-[2-(benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Stage #1: (S)-2-{1-[2-(benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide With hydrogen; acetic acid; palladium 10% on activated carbon at 40℃; under 760.051 Torr; for 6h; Stage #2: With sodium hydroxide In dichloromethane; water Product distribution / selectivity;

: 133034-08-9
3-(S)-(-)-(1-carbamoyl-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)-2-oxoethyl]-pyrrolidine hydrochloride

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Stage #1: 3-(S)-(-)-(1-carbamoyl-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)-2-oxoethyl]-pyrrolidine hydrochloride With hydrogen; acetic acid; 5%-palladium/activated carbon at 80 - 90℃; for 7 - 8h; Stage #2: With sodium hydroxide; water pH=10;

: 1072227-73-6
2,2-diphenyl-2-{(S)-1-[2-(2,3-dihydro-benzofuran-5-yl)-ethyl]-pyrrolidin-3-yl}-acetic acid methyl ester

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
With ammonia In methanol at 28 - 45℃; for 5 - 7h; Product distribution / selectivity;

: 127264-14-6
2,3-dihydro-5-(2-bromoethyl)benzofuran

: (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Stage #1: (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium carbonate In water at 25 - 30℃; for 0.5h; Stage #2: 2,3-dihydro-5-(2-bromoethyl)benzofuran In water at 25 - 75℃; for 12h;
With potassium hydroxide In acetonitrile at 25 - 45℃; Product distribution / selectivity;

: 133099-07-7
(S)-darifenacin hydrobromide

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
With sodium hydroxide In water at 20 - 25℃; pH=12;

: 1189753-52-3
(S)-2,2-diphenyl-2-[1-(tert-butyloxycarbonyl)-3-pyrrolidinyl]acetonitrile

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / methanol / 7 h / 20 - 30 °C 2.1: sulfuric acid / 12 h / 85 - 90 °C 3.1: ethanol / 1 h 4.1: potassium carbonate / water / 0.5 h / 25 - 30 °C 4.2: 12 h / 25 - 75 °C View Scheme

: 133099-11-3
(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / 12 h / 85 - 90 °C 2.1: ethanol / 1 h 3.1: potassium carbonate / water / 0.5 h / 25 - 30 °C 3.2: 12 h / 25 - 75 °C View Scheme
Multi-step reaction with 2 steps 1.1: sulfuric acid / 10 h / 95 - 100 °C 1.2: 25 - 30 °C 2.1: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 16 h / 80 °C 1.2: 0.5 h 2.1: potassium tert-butylate / tert-Amyl alcohol; water / 20 h / 110 °C / Inert atmosphere 2.2: 24 h / 110 °C / Inert atmosphere View Scheme

: 90843-31-5
1-(2,3-dihydrobenzofuran-5-yl)ethanone

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / methanol / 0.5 h / 0 - 5 °C 1.2: 6 h / 0 - 5 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 5 - 10 °C / Inert atmosphere 2.2: 4 h / 45 - 50 °C / Inert atmosphere 3.1: potassium carbonate / water / 0.5 h / 25 - 30 °C 3.2: 12 h / 25 - 75 °C View Scheme

: 151427-19-9
2-bromo-1-(2,3-dihydrobenzofuran-5-yl)ethan-1-one

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 5 - 10 °C / Inert atmosphere 1.2: 4 h / 45 - 50 °C / Inert atmosphere 2.1: potassium carbonate / water / 0.5 h / 25 - 30 °C 2.2: 12 h / 25 - 75 °C View Scheme

: 496-16-2
2,3-Dihydrobenzofuran

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 1.2: 0.5 h / 0 - 5 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / methanol / 0.5 h / 0 - 5 °C 2.2: 6 h / 0 - 5 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 5 - 10 °C / Inert atmosphere 3.2: 4 h / 45 - 50 °C / Inert atmosphere 4.1: potassium carbonate / water / 0.5 h / 25 - 30 °C 4.2: 12 h / 25 - 75 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere
1.2: 0.5 h / 0 - 5 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / methanol / 0.5 h / 0 - 5 °C
2.2: 6 h / 0 - 5 °C
3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 5 - 10 °C / Inert atmosphere
3.2: 4 h / 45 - 50 °C / Inert atmosphere
4.1: potassium carbonate / water / 0.5 h / 25 - 30 °C
4.2: 12 h / 25 - 75 °C
View Scheme

: 943034-50-2
2-(2,3-dihydrobenzofuran-5-yl)ethylchloride

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium bromide / acetone / 48 h / Heating / reflux 2: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C View Scheme
Multi-step reaction with 3 steps 1: sodium bromide / acetone / 48 h / Heating / reflux 2: potassium carbonate / acetonitrile 3: ammonia / methanol / 5 - 7 h / 28 - 45 °C View Scheme

: 127264-14-6
2,3-dihydro-5-(2-bromoethyl)benzofuran

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile 2: ammonia / methanol / 5 - 7 h / 28 - 45 °C View Scheme

: (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 0.33 h / 25 - 60 °C / pH 12 - 14 2: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C View Scheme

: 133099-09-9
(S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen bromide / water; phenol / 4 h / Heating / reflux 2.1: sulfuric acid / 10 h / 95 - 100 °C 2.2: 25 - 30 °C 3.1: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C View Scheme

: 1072227-71-4
2,2-diphenyl-2-((S)-pyrrolidin-3-yl)-acetic acid methyl ester

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile 2: ammonia / methanol / 5 - 7 h / 28 - 45 °C View Scheme

: 1072227-66-7
methyl 2,2-diphenyl-2-((S)-1-tosyl-pyrrolidin-3-yl)-acetate

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen bromide; acetic acid 2: potassium carbonate / acetonitrile 3: ammonia / methanol / 5 - 7 h / 28 - 45 °C View Scheme

: 86-29-3
Diphenylacetonitrile

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 2 h 1.2: 5 h / 95 - 100 °C 2.1: hydrogen bromide / water; phenol / 4 h / Heating / reflux 3.1: sulfuric acid / 10 h / 95 - 100 °C 3.2: 25 - 30 °C 4.1: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C View Scheme

: 3469-00-9
methyl 2,2-diphenylacetate

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / toluene / 1 h / 55 - 60 °C 1.2: 3 h / 25 - 30 °C / Heating / reflux 2.1: hydrogen bromide; acetic acid 3.1: potassium carbonate / acetonitrile 4.1: ammonia / methanol / 5 - 7 h / 28 - 45 °C View Scheme

: 64089-34-5
2-chloro-1-(2,3-dihydrobenzofuran-5-yl)ethanone

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; sulfuric acid / tetrahydrofuran / 10 h / -5 - 0 °C 2: sodium bromide / acetone / 48 h / Heating / reflux 3: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C View Scheme
Multi-step reaction with 4 steps 1: sodium tetrahydroborate; sulfuric acid / tetrahydrofuran / 10 h / -5 - 0 °C 2: sodium bromide / acetone / 48 h / Heating / reflux 3: potassium carbonate / acetonitrile 4: ammonia / methanol / 5 - 7 h / 28 - 45 °C View Scheme

: C2H2O4*C18H18N2

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 0.25 h / 50 - 60 °C / pH 12 2.1: sulfuric acid / 10 h / 95 - 100 °C 2.2: 25 - 30 °C 3.1: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C View Scheme

: 1190695-09-0
(3R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-ol

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triphenylphosphine; benzoic acid; diethylazodicarboxylate / toluene / 0 - 20 °C 1.2: 5 h / 20 °C 2.1: triethylamine / dichloromethane / -10 - 20 °C 3.1: sodium hydride / toluene / 2 h / Reflux 3.2: 9 h / Reflux 4.1: tetrabutylammomium bromide; potassium hydroxide / iso-butanol / 48 h / Reflux View Scheme

: 1190695-10-3
(S)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3-hydroxypyrrolidine

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / -10 - 20 °C 2.1: sodium hydride / toluene / 2 h / Reflux 2.2: 9 h / Reflux 3.1: tetrabutylammomium bromide; potassium hydroxide / iso-butanol / 48 h / Reflux View Scheme

: 1190695-11-4
(S)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3-p-toluenesulfonylpyrrolidine

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / toluene / 2 h / Reflux 1.2: 9 h / Reflux 2.1: tetrabutylammomium bromide; potassium hydroxide / iso-butanol / 48 h / Reflux View Scheme

: 134002-25-8
2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide

: 133099-04-4
darifenacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 - 60 °C 2: potassium hydroxide / acetonitrile / 25 - 45 °C View Scheme

: 133099-04-4
darifenacin

: 133099-07-7
(S)-darifenacin hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide In water; acetone at 0 - 20℃; for 7h;	75%
With hydrogen bromide In water; acetone	65%
With hydrogen bromide In water; acetone for 1.25 - 2.33333h; Product distribution / selectivity;

: 133099-04-4
darifenacin

: 586346-94-3
darifenacin hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 0 - 30℃; for 12h; Product distribution / selectivity;
With hydrogenchloride In water; acetone at 0 - 30℃; for 12h;

Darifenacin Specification

1. Introduction of Darifenacin

Darifenacin, with the IUPAC Name of 2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide, is one kind of medication used to treat urinary incontinence. This chemical belongs to the Product Categories which include Pharmaceutical material and intermeidates; API.

2. Properties of Darifenacin

Darifenacin has the following property datas: (1)Index of Refraction: 1.624; (2)Molar Refractivity: 126.32 cm³; (3)Molar Volume: 357.7 cm³; (4)Polarizability: 50.08×10-24cm³; (5)Surface Tension: 53 dyne/cm; (6)Density: 1.192 g/cm³; (7)Flash Point: 325.3 °C; (8)Enthalpy of Vaporization: 91.16 kJ/mol; (9)Boiling Point: 614.3 °C at 760 mmHg; (10)Vapour Pressure: 5E-15 mmHg at 25°C.

3. Structure Descriptors of Darifenacin

You could convert the following datas into the molecular structure:
(1). Canonical SMILES: C1CN(CC1C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N)CCC4=CC5=C(C=C4)OCC5
(2). Isomeric SMILES: C1CN(C[C@@H]1C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N)CCC4=CC5=C(C=C4)OCC5
(3). InChI: InChI=1S/C28H30N2O2/c29-27(31)28(23-7-3-1-4-8-23,24-9-5-2-6-10-24)25-14-17-30(20-25)16-13-21-11-12-26-22(19-21)15-18-32-26/h1-12,19,25H,13-18,20H2,(H2,29,31)/t25-/m1/s1
(4). InChIKey: HXGBXQDTNZMWGS-RUZDIDTESA-N

Product Name

Darifenacin

Synthetic route

Darifenacin Specification

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