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Basic Information
CAS No.: 148849-67-6
Name: Ivabradine hydrochloride
Article Data: 24
Molecular Structure:
Molecular Structure of 148849-67-6 (Ivabradine hydrochloride)
Formula: C27H36N2O5.HCl
Molecular Weight: 505.054
Synonyms: 2H-3-Benzazepin-2-one,3-[3-[[(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-,monohydrochloride, (S)-;
EINECS: 638-798-3
Melting Point: 193-196?C
Boiling Point: 626.9 °C at 760 mmHg
Flash Point: 332.9 °C
Hazard Symbols: N
Risk Codes: 50/53
Safety: 60-61
PSA: 60.47000
LogP: 4.04990
Related products
Synthetic route
1086026-31-4

3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
Stage #1: 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium 10% on activated carbon; hydrogen; acetic acid at 15 - 25℃; for 23h;
Stage #2: With hydrogenchloride In ethyl acetate; isopropyl alcohol at 0 - 10℃; for 1h;		93.5%
Stage #1: 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium 10% on activated carbon; hydrogen; ammonium formate In methanol at 25 - 30℃;
Stage #2: With hydrogenchloride In dichloromethane		78%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In water at 45℃; under 7500.75 Torr; for 6h;
Multi-step reaction with 2 steps
1: hydrogenchloride / acetonitrile / 20 - 25 °C
2: 5%-palladium/activated carbon; hydrogen / methanol / 18 h / 30 - 35 °C / 3000.3 - 3750.38 Torr / Autoclave
View Scheme
Stage #1: 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium 10% on activated carbon; hydrogen In methanol at 25 - 30℃; under 5250.53 - 6000.6 Torr;
Stage #2: With hydrogenchloride In dichloromethane; water		24.48 g

3-(2-[1,3]-dioxolan-2-yl-ethyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
Stage #1: 3-(2-[1,3]-dioxolan-2-yl-ethyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With hydrogen; palladium on activated charcoal In ethanol at 55℃; under 3750.38 Torr;
Stage #2: 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride In ethanol; water at 20 - 85℃; under 22502.3 Torr;		85%
Stage #1: 3-(2-[1,3]-dioxolan-2-yl-ethyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium on activated charcoal; hydrogen In ethanol at 55℃; under 3750.38 Torr; Autoclave; Large scale;
Stage #2: 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride With palladium on activated charcoal; hydrogen In ethanol; water at 85℃; under 22502.3 Torr; Autoclave; Large scale;		85%
Stage #1: 3-(2-[1,3]-dioxolan-2-yl-ethyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium on activated charcoal; hydrogen In ethanol at 20 - 55℃; under 3750380 Torr; Autoclave; Inert atmosphere;
Stage #2: 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride In ethanol; water at 20 - 85℃; under 63756400 Torr; Inert atmosphere;		85%

3-[2-(1,3-Dioxolan-2-yl)-ethyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethanol; water at 85℃; under 22502.3 Torr; Autoclave;85%
155974-00-8

ivabradine

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; acetonitrile at 20℃; pH=2;81%
With hydrogenchloride In acetonitrile at 60℃; pH=2 - 3;80.1%
With hydrogenchloride In diethyl ether; acetonitrile Product distribution / selectivity;78%
1086026-38-1

3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino)propyl]-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one hydrochloride

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol at 30 - 35℃; under 3000.3 - 3750.38 Torr; for 18h; Autoclave;80%
866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
1.2: 2 h / 20 °C
2.1: potassium carbonate / water / 0.08 h
2.2: Inert atmosphere
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / acetonitrile / 12 h / 20 °C
2: hydrogenchloride; pyrographite / acetonitrile / 0.17 h / 70 °C / pH 2 - 3
View Scheme
35202-54-1

3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: potassium hydroxide; water / 4 h / Reflux
1.2: 20 °C
2.1: ethyl acetate / 1.25 h / 0 °C / Reflux
3.1: hydrogenchloride / dichloromethane; water / 0.08 h
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
5.1: dichloromethane; water / 0 - 10 °C
6.1: borane-THF / tetrahydrofuran / 20 - 50 °C
6.2: 0.25 h / 0 - 5 °C
6.3: 2.5 h / 0 °C / Reflux
7.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
7.2: 2 h / 20 °C
8.1: potassium carbonate / water / 0.08 h
8.2: Inert atmosphere
9.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 9 steps
1.1: potassium hydroxide; water / 4 h / Reflux
1.2: 20 °C
2.1: acetone / 0.5 h / Reflux; Cooling
3.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
5.1: dichloromethane; water / 0 - 10 °C
6.1: borane-THF / tetrahydrofuran / 20 - 50 °C
6.2: 0.25 h / 0 - 5 °C
6.3: 2.5 h / 0 °C / Reflux
7.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
7.2: 2 h / 20 °C
8.1: potassium carbonate / water / 0.08 h
8.2: Inert atmosphere
9.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 9 steps
1.1: potassium hydroxide; water / 4 h / Reflux
1.2: 20 °C
2.1: ethyl acetate / 1 h / 18 °C / Heating
3.1: hydrogenchloride / dichloromethane; water / 0.33 h
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
5.1: dichloromethane; water / 0 - 10 °C
6.1: borane-THF / tetrahydrofuran / 20 - 50 °C
6.2: 0.25 h / 0 - 5 °C
6.3: 2.5 h / 0 °C / Reflux
7.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
7.2: 2 h / 20 °C
8.1: potassium carbonate / water / 0.08 h
8.2: Inert atmosphere
9.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
41234-23-5

(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: ethyl acetate / 1.25 h / 0 °C / Reflux
2.1: hydrogenchloride / dichloromethane; water / 0.08 h
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
6.2: 2 h / 20 °C
7.1: potassium carbonate / water / 0.08 h
7.2: Inert atmosphere
8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 8 steps
1.1: acetone / 0.5 h / Reflux; Cooling
2.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
6.2: 2 h / 20 °C
7.1: potassium carbonate / water / 0.08 h
7.2: Inert atmosphere
8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 8 steps
1.1: ethyl acetate / 1 h / 18 °C / Heating
2.1: hydrogenchloride / dichloromethane; water / 0.33 h
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
6.2: 2 h / 20 °C
7.1: potassium carbonate / water / 0.08 h
7.2: Inert atmosphere
8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 8 steps
1.1: ethyl acetate / 1 h / 18 °C / Heating
2.1: hydrogenchloride / dichloromethane; water / 0.33 h
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
6.2: 2 h / 20 °C
7.1: potassium carbonate / water / 0.08 h
7.2: Inert atmosphere
8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 8 steps
1.1: ethyl acetate / Heating
2.1: hydrogenchloride / dichloromethane; water / 0.33 h
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
6.2: 2 h / 20 °C
7.1: potassium carbonate / water / 0.08 h
7.2: Inert atmosphere
8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme

(S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid (+)-cinchonine

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: hydrogenchloride / dichloromethane; water / 0.08 h
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
3.1: dichloromethane; water / 0 - 10 °C
4.1: borane-THF / tetrahydrofuran / 20 - 50 °C
4.2: 0.25 h / 0 - 5 °C
4.3: 2.5 h / 0 °C / Reflux
5.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
5.2: 2 h / 20 °C
6.1: potassium carbonate / water / 0.08 h
6.2: Inert atmosphere
7.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
1220993-44-1

(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid

148849-67-6

ivabradine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
2.1: dichloromethane; water / 0 - 10 °C
3.1: borane-THF / tetrahydrofuran / 20 - 50 °C
3.2: 0.25 h / 0 - 5 °C
3.3: 2.5 h / 0 °C / Reflux
4.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
4.2: 2 h / 20 °C
5.1: potassium carbonate / water / 0.08 h
5.2: Inert atmosphere
6.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 3 steps
1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 20 °C
1.2: 20 °C
2.1: borane-THF / tetrahydrofuran / 20 °C
2.2: 4 h
3.1: hydrogen; palladium on activated charcoal / ethanol / 55 °C / 3750.38 Torr / Autoclave; Large scale
3.2: 85 °C / 22502.3 Torr / Autoclave; Large scale
View Scheme
Raw Materials
866783-12-2
41234-23-5
85175-65-1
155974-00-8
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35202-54-1
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Chemistry

Molecular Structure of Ivabradine HCl (CAS NO.148849-67-6):

IUPAC Name: 3-[3-[[(7S)-3,4-Dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl]methyl-methylamino]propyl]-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one hydrochloride 
Molecular Formula: C27H36N2O5.HCl
Molecular Weight: 505.05
H-Bond Donor: 1
H-Bond Acceptor: 6 
Flash Point: 332.9 °C
Enthalpy of Vaporization: 92.79 kJ/mol
Boiling Point: 626.9 °C at 760 mmHg
Vapour Pressure: 1.24E-15 mmHg at 25 °C
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals 
SMILES: Cl.O=C2N(CCc1cc(OC)c(OC)cc1C2)CCCN(C[C@@H]4c3cc(OC)c(OC)cc3C4)C
InChI: InChI=1/C27H36N2O5.ClH/c1-28(17-21-11-20-14-25(33-4)26(34-5)16-22(20)21)8-6-9-29-10-7-18-12-23(31-2)24(32-3)13-19(18)15-27(29)30;/h12-14,16,21H,6-11,15,17H2,1-5H3;1H/t21-;/m1./s1
InChIKey: HLUKNZUABFFNQS-ZMBIFBSDBJ

Uses

 Ivabradine HCl (CAS NO.148849-67-6) is used as selective bradycardic agent with direct effect on the pacemake, if current of the sinoatrial node.

Specification

 Ivabradine HCl (CAS NO.148849-67-6), its Synonyms are (7,8-Dimethoxy 3-(3-(((1S)-(4,5-dimethoxybenzocyclobutan-1-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-2H-benzazepin-2-one hydrochloride ; Ivabradine hydrochloride ; 2H-3-Benzazepin-2-one, 3-(3-((((7S)-3,4-dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-, monohydrochloride ; 2H-3-Benzazepin-2-one, 3-(3-(((3,4-dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-, monohydrochloride, (S)- .