Product Name

  • Name

    Darifenacin hydrobromide

  • EINECS 603-705-7
  • CAS No. 133099-07-7
  • Article Data14
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 228-230 °C
  • Formula C28H30N2O2.HBr
  • Boiling Point 614.3 °C at 760 mmHg
  • Molecular Weight 507.47
  • Flash Point 325.3 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 133099-07-7 (Darifenacin hydrobromide)
  • Hazard Symbols
  • Synonyms 2-[(3S)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenyl-acetamide hydrobromide;Enablex (TN);3-Pyrrolidineacetamide, 1-(2-(2,3-dihydro-5-benzofuranyl)ethyl)-alpha,alpha-diphenyl-, monohydrobromide, (S)-;Enablex;Darifenacin HBr;
  • PSA 41.57000
  • LogP 5.94630

Synthetic route

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

2,3-dihydro-5-(2-bromoethyl)benzofuran

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

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

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
133033-99-5

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

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

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

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
943034-50-2

2-(2,3-dihydrobenzofuran-5-yl)ethylchloride

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

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

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
133099-04-4

darifenacin

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In water; acetone at 0 - 20℃; for 7h;75%
With hydrogen bromide In water; acetone65%
With hydrogen bromide In water; acetone for 1.25 - 2.33333h; Product distribution / selectivity;
(-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide

(-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
943034-50-2

2-(2,3-dihydrobenzofuran-5-yl)ethylchloride

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

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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)-darifenamine

(S)-darifenamine

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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;
darifenacin hydrobromide

darifenacin hydrobromide

A

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

B

(3R)-2-{1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide hydrobromide
1092800-15-1

(3R)-2-{1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide hydrobromide

Conditions
ConditionsYield
Purification / work up; Resolution of enanthiomeric mixture;A 50.8 - 51.8 %Chromat.
B 48.0 - 49.0 %Chromat.
(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate

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

2-(2,3-dihidrobenzofuran-5-yl)ethyl tosylate
79679-49-5

2-(2,3-dihidrobenzofuran-5-yl)ethyl tosylate

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
87776-76-9

5-(2-hydroxyethyl)-2,3-dihydrobenzofuran

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
1189753-52-3

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

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
133099-11-3

(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
134002-25-8

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
90843-31-5

1-(2,3-dihydrobenzofuran-5-yl)ethanone

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
151427-19-9

2-bromo-1-(2,3-dihydrobenzofuran-5-yl)ethan-1-one

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
496-16-2

2,3-Dihydrobenzofuran

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
943034-50-2

2-(2,3-dihydrobenzofuran-5-yl)ethylchloride

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate

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

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
133099-09-9

(S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
1072227-71-4

2,2-diphenyl-2-((S)-pyrrolidin-3-yl)-acetic acid methyl ester

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
1072227-66-7

methyl 2,2-diphenyl-2-((S)-1-tosyl-pyrrolidin-3-yl)-acetate

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
1072227-73-6

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

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
86-29-3

Diphenylacetonitrile

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
3469-00-9

methyl 2,2-diphenylacetate

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
64089-34-5

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

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
C2H2O4*C18H18N2

C2H2O4*C18H18N2

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
1190695-09-0

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

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
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
133099-07-7

(S)-darifenacin hydrobromide

darifenacin
133099-04-4

darifenacin

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

Darifenacin hydrobromide Chemical Properties

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 Specification

 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)- .

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