2,3-dihydro-5-(2-bromoethyl)benzofuran
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium hydroxide; triethylmethylammonium chloride In water; toluene at 100℃; for 15.25h; Stage #2: With hydrogen bromide In water; toluene Product distribution / selectivity; | 93.2% |
Stage #1: (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium hydroxide; triethylmethylammonium chloride In 2-methyltetrahydrofuran; water at 60 - 70℃; Stage #2: 2,3-dihydro-5-(2-bromoethyl)benzofuran In 2-methyltetrahydrofuran; water for 16h; Heating / reflux; Stage #3: With hydrogen bromide In 2-methyltetrahydrofuran; water at 0 - 20℃; for 2h; Product distribution / selectivity; | 90.67% |
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium hydroxide; triethylmethylammonium chloride In water; butanone at 75℃; for 6h; Stage #2: With hydrogen bromide In water; butanone at 0 - 5℃; for 2h; Product distribution / selectivity; | 84.92% |
(S)-2-{1-[2-(benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide
(S)-darifenacin hydrobromide
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 45 - 50℃; for 6 - 7h; Stage #2: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity; | 85% |
2,3-dihydro-5-(2-bromoethyl)benzofuran
2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium hydroxide; triethylmethylammonium chloride In water; butanone at 75℃; for 6h; Heating / reflux; Stage #2: With hydrogen bromide In water; butanone | 84.92% |
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium carbonate In acetonitrile at 70 - 75℃; for 2h; Stage #2: With hydrogen bromide In water; acetone at 0 - 25℃; Product distribution / selectivity; | |
With potassium carbonate In acetonitrile |
2-(2,3-dihydrobenzofuran-5-yl)ethylchloride
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Stage #1: 2-(2,3-dihydrobenzofuran-5-yl)ethylchloride; (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium carbonate In water at 101 - 103℃; for 2.5 - 5h; Stage #2: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity; | 77.2% |
darifenacin
(S)-darifenacin hydrobromide
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; |
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Stage #1: (-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide With potassium hydroxide; tert-Amyl alcohol at 60℃; for 22 - 23h; Heating / reflux; Stage #2: With hydrogen bromide In water; butanone Product distribution / selectivity; | 72% |
Stage #1: (-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide With potassium hydroxide In tert-Amyl alcohol at 60 - 108℃; Stage #2: With water Stage #3: With hydrogen bromide In acetic acid; acetone at 20℃; | 72% |
Stage #1: (-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide With potassium hydroxide In iso-butanol at 105 - 110℃; for 50h; Stage #2: With hydrogen bromide; acetic acid In acetone for 1h; Stage #3: With sodium hydroxide; water; hydrogen bromide; acetic acid Product distribution / selectivity; more than 3 stages; | 27.5% |
2-(2,3-dihydrobenzofuran-5-yl)ethylchloride
2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With sodium hydroxide; water In ethyl acetate at 25 - 35℃; for 0.25h; Stage #2: 2-(2,3-dihydrobenzofuran-5-yl)ethylchloride With triethylamine at 95℃; for 15h; Stage #3: With hydrogen bromide In water; acetone for 1h; Product distribution / selectivity; | 70% |
Stage #1: 2-(2,3-dihydrobenzofuran-5-yl)ethylchloride; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium carbonate In water at 101 - 103℃; for 2 - 5h; Stage #2: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity; |
2,3-dihydro-5-(2-bromoethyl)benzofuran
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C 2: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile 2: ammonia / methanol / 5 - 7 h / 28 - 45 °C 3: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Stage #1: (S)-darifenamine With sodium tetrahydroborate In ethanol at 20℃; for 3h; Stage #2: With water In ethanol Stage #3: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity; |
A
(S)-darifenacin hydrobromide
B
(3R)-2-{1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide hydrobromide
Conditions | Yield |
---|---|
Purification / work up; Resolution of enanthiomeric mixture; | A 50.8 - 51.8 %Chromat. B 48.0 - 49.0 %Chromat. |
2-(2,3-dihidrobenzofuran-5-yl)ethyl tosylate
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Stage #1: (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate; 2-(2,3-dihidrobenzofuran-5-yl)ethyl tosylate With potassium carbonate In acetonitrile at 25 - 70℃; Inert atmosphere; Stage #2: With hydrogen bromide In dichloromethane; water at 5 - 30℃; pH=2 - 9; |
5-(2-hydroxyethyl)-2,3-dihydrobenzofuran
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere 2.1: potassium carbonate / acetonitrile / 25 - 70 °C / Inert atmosphere 2.2: 5 - 30 °C / pH 2 - 9 View Scheme |
(S)-2,2-diphenyl-2-[1-(tert-butyloxycarbonyl)-3-pyrrolidinyl]acetonitrile
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 5.1: hydrogen bromide / water; acetone / 7 h / 0 - 20 °C View Scheme |
(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 4 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 4.1: hydrogen bromide / water; acetone / 7 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 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 3.1: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ethanol / 1 h 2.1: potassium carbonate / water / 0.5 h / 25 - 30 °C 2.2: 12 h / 25 - 75 °C 3.1: hydrogen bromide / water; acetone / 7 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C 2: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme | |
Multi-step reaction with 3 steps 1: water / 50 - 60 °C 2: potassium hydroxide / acetonitrile / 25 - 45 °C 3: hydrogen bromide / acetone / 10 - 25 °C View Scheme |
1-(2,3-dihydrobenzofuran-5-yl)ethanone
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 4 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 4.1: hydrogen bromide / water; acetone / 7 h / 0 - 20 °C View Scheme |
2-bromo-1-(2,3-dihydrobenzofuran-5-yl)ethan-1-one
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 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 3.1: hydrogen bromide / water; acetone / 7 h / 0 - 20 °C View Scheme |
2,3-Dihydrobenzofuran
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 5.1: hydrogen bromide / water; acetone / 7 h / 0 - 20 °C View Scheme |
2-(2,3-dihydrobenzofuran-5-yl)ethylchloride
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium bromide / acetone / 48 h / Heating / reflux 2: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C 3: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme | |
Multi-step reaction with 4 steps 1: sodium bromide / acetone / 48 h / Heating / reflux 2: potassium carbonate / acetonitrile 3: ammonia / methanol / 5 - 7 h / 28 - 45 °C 4: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 0.33 h / 25 - 60 °C / pH 12 - 14 2: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C 3: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
(S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 4 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 4.1: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
2,2-diphenyl-2-((S)-pyrrolidin-3-yl)-acetic acid methyl ester
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile 2: ammonia / methanol / 5 - 7 h / 28 - 45 °C 3: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
methyl 2,2-diphenyl-2-((S)-1-tosyl-pyrrolidin-3-yl)-acetate
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogen bromide; acetic acid 2: potassium carbonate / acetonitrile 3: ammonia / methanol / 5 - 7 h / 28 - 45 °C 4: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
2,2-diphenyl-2-{(S)-1-[2-(2,3-dihydro-benzofuran-5-yl)-ethyl]-pyrrolidin-3-yl}-acetic acid methyl ester
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ammonia / methanol / 5 - 7 h / 28 - 45 °C 2: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
Diphenylacetonitrile
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 5.1: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
methyl 2,2-diphenylacetate
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 5.1: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
2-chloro-1-(2,3-dihydrobenzofuran-5-yl)ethanone
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
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 hydroxide / acetonitrile / 18 h / 40 - 50 °C 4: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme | |
Multi-step reaction with 5 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 5: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 4 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 4.1: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
(3R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-ol
(S)-darifenacin hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 5.1: hydrogen bromide / water; acetone View Scheme |
(S)-darifenacin hydrobromide
darifenacin
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20 - 25℃; pH=12; |
Product Name: Darifenacin hydrobromide (CAS NO.133099-07-7)
Molecular Formula: C28H30N2O2.HBr
Molecular Weight: 507.47g/mol
Mol File: 133099-07-7.mol
Boiling point: 614.3 °C at 760 mmHg
Flash Point: 325.3 °C
Enthalpy of Vaporization: 91.16 kJ/mol
Vapour Pressure: 5E-15 mmHg at 25°C
H-Bond Donor: 1
H-Bond Acceptor: 3
Structure Descriptors of Darifenacin hydrobromide (CAS NO.133099-07-7):
IUPAC Name: 2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide hydrobromide
Canonical SMILES: C1CN(CC1C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N)CCC4=CC5=C(C=C4)OCC5.Br
Isomeric SMILES: C1CN(C[C@@H]1C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N)CCC4=CC5=C(C=C4)OCC5.Br
InChI: InChI=1S/C28H30N2O2.BrH/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);1H/t25-;/m1./s1
InChIKey: UQAVIASOPREUIT-VQIWEWKSSA-N
Product Categories: APIs; Intermediates & Fine Chemicals; Pharmaceuticals
Darifenacin hydrobromide , its CAS NO. is 133099-07-7, the synonyms are (S)-2-{1-(2-(2,3-Dihydrobenzofuran-5-yl)ethyl)-3-pyrrolidnyl}-2,2-diphenylacetamide hydrobromide ; 3-Pyrrolidineacetamide, 1-(2-(2,3-dihydro-5-benzofuranyl)ethyl)-alpha,alpha-diphenyl-, monohydrobromide, (3S)- .
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View