CAS No.133099-07-7,Darifenacin hydrobromide Suppliers

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Basic Information

Molecular Structure:
CAS No.:	133099-07-7
Name:	Darifenacin hydrobromide
Article Data:	14

Formula:	C₂₈H₃₀N₂O₂^.HBr
Molecular Weight:	507.47
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;
EINECS:	603-705-7
Melting Point:	228-230 °C
Boiling Point:	614.3 °C at 760 mmHg
Flash Point:	325.3 °C
PSA:	41.57000
LogP:	5.94630

Synthetic route

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

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

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

Conditions

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%

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

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

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 45 - 50℃; for 6 - 7h; Stage #2: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity;	85%

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

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

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

Conditions

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

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

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

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

Conditions

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%

: 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;

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

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

Conditions

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%

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

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

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

Conditions

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;

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

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

Conditions

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)-darifenamine

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

Conditions

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;

: darifenacin hydrobromide

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

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

Conditions

Conditions	Yield
Purification / work up; Resolution of enanthiomeric mixture;	A 50.8 - 51.8 %Chromat. B 48.0 - 49.0 %Chromat.

Raw Materials

496-16-2

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Chemistry

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

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)- .