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103129-82-4

Basic Information
CAS No.: 103129-82-4
Name: (S)-Amlodipine
Molecular Structure:
Molecular Structure of 103129-82-4 ((S)-Amlodipine)
Formula: C20H25ClN2O5
Molecular Weight: 408.88
Synonyms: 3,5-Pyridinedicarboxylicacid, 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-,3-ethyl 5-methyl ester, (S)-;(-)-Amlodipine;(S)-(-)-Amlodipine;Levamlodipine;Levoamlodipine;Lodien;l-Amlodipine;
EINECS: 1592732-453-0
Density: 1.227 g/cm3
Melting Point: 102-104°C
Boiling Point: 527.2 °C at 760 mmHg
Flash Point: 272.6 °C
Solubility:
Appearance: white crystal powder
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 99.88000
LogP: 3.29540
Synthetic route

S-(-)-amlodipine-hemi-D-tartrate mono-dimethylsulfoxide solvate

103129-82-4

amlodipine

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 20℃; for 0.666667h;93.9%

2C20H25ClN2O5*C24H17NO10

103129-82-4

amlodipine

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 20℃; for 0.5h;93%

S(-) amlodipine-hemi L(+)-tartarate mono DMSO solvate

103129-82-4

amlodipine

Conditions
ConditionsYield
With ammonia; water In dichloromethane for 0.5h; Product distribution / selectivity;92%
88150-42-9

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

103129-82-4

amlodipine

Conditions
ConditionsYield
Stage #1: 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With D-(+)-camphoric acid In isopropyl alcohol at 20℃; for 12.5h;
Stage #2: With sodium hydroxide In dichloromethane; water for 1h; Reagent/catalyst;
90.5%
With D-tartaric acid In dimethyl sulfoxide; acetone at 20 - 60℃; for 1.5h; Reagent/catalyst; Solvent;45.2%
Stage #1: 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With L-Tartaric acid In ISOPROPYLAMIDE at 5℃; for 2h; Resolution of racemate;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.666667h;
n/a
Multi-step reaction with 2 steps
1: water; iso-butanol / 1 h / 50 °C
2: sodium hydroxide / dichloromethane; water / pH 9
View Scheme

S-(-)-amlodipine D-(-)-tartrate urea complex

103129-82-4

amlodipine

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water pH=9;90%
With sodium hydroxide In dichloromethane; water pH=9;90%

S(-) amlodipine-hemi-L-(+) tartarate monohydrate

103129-82-4

amlodipine

Conditions
ConditionsYield
With ammonia; water In dichloromethane for 0.5h; Product distribution / selectivity;82%
147-71-7

D-tartaric acid

88150-42-9

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

(R)-amlodipine-D-hemitartrate dimethylformamide solvate

B

103129-82-4

amlodipine

Conditions
ConditionsYield
In water at 20℃; for 4.5h; Product distribution / selectivity;A 78.38%
B n/a

(S)-(-)-amlodipine-hemi-L-tartrate

103129-82-4

amlodipine

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water at 5℃; for 0.333333h;69%
143191-87-1

(-)-2-<<2-<(tert-butoxycarbonyl)amino>ethoxy>-methyl>-4-(2-chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridine

103129-82-4

amlodipine

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; acetonitrile for 1h;64%
125711-60-6

2-<(2-azidoethoxy)methyl>-4(S)-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-1,4-dihydropyridine

103129-82-4

amlodipine

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In ethanol under 775.7 Torr; Yield given;
With sodium tetrahydroborate; nickel dichloride In ethanol Ambient temperature; Yield given;

(1R,3S)-camphoric acid salt of S-amlodipine

A

103129-81-3

(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

B

103129-82-4

amlodipine

Conditions
ConditionsYield
With sodium hydroxide; water In dichloromethane

S(-) amlodipine hemi D(-) tartarate

103129-82-4

amlodipine

Conditions
ConditionsYield
With sodium hydroxide In tert-butyl methyl ether at 20 - 25℃; for 0.5h;
103069-49-4

2-<(2-azidoethoxy)methyl>-4-(2-chlorophenyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

103129-82-4

amlodipine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) carbonyldiimidazole / 1.) CH2Cl2, reflux, 2.) THF, RT, 1 h
2: NaOEt / bis-(2-methoxy-ethyl) ether / 1 h / Heating
3: H2 / 5percent Pd/CaCO3 / ethanol / 775.7 Torr
View Scheme
Multi-step reaction with 3 steps
1: 1.) carbonyldiimidazole
2: ethanol / 1 h / Heating
3: 6percent nickel chloride, sodium borohydride / ethanol / Ambient temperature
View Scheme
103094-34-4

(+)-2-<(2-azidoethoxy)methyl>-4-(2-chlorophenyl)-5-(methoxycarbonyl)-3-<(2(S)-methoxy-2-phenethoxy)carbonyl>-6-methyl-1,4-dihydropyridine

103129-82-4

amlodipine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOEt / bis-(2-methoxy-ethyl) ether / 1 h / Heating
2: H2 / 5percent Pd/CaCO3 / ethanol / 775.7 Torr
View Scheme
Multi-step reaction with 2 steps
1: ethanol / 1 h / Heating
2: 6percent nickel chloride, sodium borohydride / ethanol / Ambient temperature
View Scheme
103069-47-2

2-cyanoethyl 4-(2-azidoethoxy)-3-oxobutanoate

103129-82-4

amlodipine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 41 percent / ethanol / 2 h / Heating
2: 74 percent / aq. NaOH / bis-(2-methoxy-ethyl) ether / 2 h / Ambient temperature
3: 1.) carbonyldiimidazole / 1.) CH2Cl2, reflux, 2.) THF, RT, 1 h
4: NaOEt / bis-(2-methoxy-ethyl) ether / 1 h / Heating
5: H2 / 5percent Pd/CaCO3 / ethanol / 775.7 Torr
View Scheme
103069-48-3

2-<(2-azidoethoxy)methyl>-4-(2-chlorophenyl)-3-(2-cyanoethoxycarbonyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

103129-82-4

amlodipine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 74 percent / aq. NaOH / bis-(2-methoxy-ethyl) ether / 2 h / Ambient temperature
2: 1.) carbonyldiimidazole / 1.) CH2Cl2, reflux, 2.) THF, RT, 1 h
3: NaOEt / bis-(2-methoxy-ethyl) ether / 1 h / Heating
4: H2 / 5percent Pd/CaCO3 / ethanol / 775.7 Torr
View Scheme
143290-24-8

2-<<2-<(tert-butoxycarbonyl)amino>ethoxy>-methyl>-4-(2-chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridine

103129-82-4

amlodipine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 64 percent / 6.7 M HCl / acetonitrile; dioxane / 1 h
View Scheme

(S)-amlodipine-hemi-D-tartrate

103129-82-4

amlodipine

Conditions
ConditionsYield
With sodium hydroxide In tert-butyl methyl ether; water; isopropyl alcohol
With sodium hydroxide In tert-butyl methyl ether; water at 20 - 25℃; for 0.333333 - 0.5h;
With sodium hydroxide In n-heptane; tert-butyl methyl ether; water at 20 - 40℃; for 2.5 - 3.5h;

L-(+)-tartaric acid

88150-42-9

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

103129-82-4

amlodipine

Conditions
ConditionsYield
Stage #1: L-(+)-tartaric acid; 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With sodium hydroxide In water; butanone at 20℃; for 1h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h;
n/a
Stage #1: L-(+)-tartaric acid; 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With sodium hydroxide In dichloromethane; butanone at 20℃; for 1h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h;
n/a
Stage #1: L-(+)-tartaric acid; 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With sodium hydroxide In ethyl acetate; butanone at 20℃; for 1h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h;
n/a
Stage #1: L-(+)-tartaric acid; 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With sodium hydroxide In ethanol; butanone at 20℃; for 1h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h;
n/a
Stage #1: L-(+)-tartaric acid; 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With sodium hydroxide In acetone; butanone at 20℃; for 1h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h;
n/a

(S)-(-)-amlodipine L-(+)-tartrate

103129-82-4

amlodipine

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water for 0.5h;n/a
88150-42-9

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

A

103129-81-3

(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

B

103129-82-4

amlodipine

Conditions
ConditionsYield
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 0℃; Purification / work up;
With isopropylamine; trifluoroacetic acid In methanol; isopropyl alcohol at 35℃; under 103432 Torr; Resolution of racemate; Supercritical conditions;
With acetic acid; triethylamine In methanol at 5℃; Reagent/catalyst; Concentration; Temperature; Resolution of racemate;
With L-glutamate based immobilized chiral ionic liquid on SBA-15 In methanol Resolution of racemate;
103129-81-3

(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

103129-82-4

amlodipine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: calcium hypochlorite / ethyl acetate; water / 20 - 30 °C
2: acetic acid; sodium cyanoborohydride / 2 h / 15 - 25 °C
3: D-tartaric acid / dimethyl sulfoxide; acetone / 1.5 h / 20 - 60 °C
View Scheme
97-67-6

(S)-Malic acid

103129-82-4

amlodipine

(S)-(-)-amlodipine L-malate salt

Conditions
ConditionsYield
In tert-butyl methyl ether; water; isopropyl alcohol at 0 - 50℃; for 4.5 - 5h;98.1%
In tert-butyl methyl ether; water; isopropyl alcohol at 50℃; for 1h; Product distribution / selectivity;98.1%
In tert-butyl methyl ether; water; isopropyl alcohol at 0 - 50℃; for 4h; Product distribution / selectivity;98.1%
103129-82-4

amlodipine

98-79-3

L-Pyroglutamic acid

851447-24-0

(S)-(-)-amlodipine pidolate salt

Conditions
ConditionsYield
In ethanol at 20℃; for 1h;97%
141-82-2

malonic acid

103129-82-4

amlodipine

851447-25-1

(S)-(-)-amlodipine malonate salt

Conditions
ConditionsYield
In ethanol at 20℃; for 1h;96%
681-57-2

2,2-dimethylglutaric acid

103129-82-4

amlodipine

(S)-(-)-amlodipin 2,2-dimethylglutarate salt

Conditions
ConditionsYield
In ethanol at 20℃; for 1h;96%
110-15-6

succinic acid

103129-82-4

amlodipine

S(-) amlodipine succinate

Conditions
ConditionsYield
In ethanol; water93%
103129-82-4

amlodipine

110-16-7

maleic acid

135969-53-8

(-)-Amlodipine maleate

Conditions
ConditionsYield
In ethanol at 25℃; for 2h; Product distribution / selectivity;91%
In water at 25℃; for 2h; Product distribution / selectivity;89%
In ethanol; water82.88%
124-04-9

Adipic acid

103129-82-4

amlodipine

S-(-)-amlodipine adipic acid salt

Conditions
ConditionsYield
In ethanol; isopropyl alcohol at 25℃; for 2h; Product distribution / selectivity;91%
In ethanol; isopropyl alcohol at 25℃; for 2h; Product distribution / selectivity;91%
In water for 5h; Product distribution / selectivity;89%
144-62-7

oxalic acid

103129-82-4

amlodipine

S(-) amlodipine oxalate

Conditions
ConditionsYield
In ethanol; water89.2%
103129-82-4

amlodipine

98-11-3

benzenesulfonic acid

150566-71-5

(-)-Amlodipine besylate

Conditions
ConditionsYield
In water; isopropyl alcohol at 20℃; for 0.5h; Product distribution / selectivity;89%
In ethanol; water at 0 - 20℃;85%
In ethanol; water Product distribution / selectivity;82.88%
In ethanol; water at 20℃; for 24h;80.2%
3144-16-9

(1S)-10-camphorsulfonic acid

103129-82-4

amlodipine

(S)-amlodipine (1S)-(+)-10-camsylate hydrate

Conditions
ConditionsYield
With water In isopropyl alcohol at 20℃; for 1h;88%
3144-16-9

(1S)-10-camphorsulfonic acid

103129-82-4

amlodipine

S-(-)-amlodipine (1S)-(+)-camphorsulfonate

Conditions
ConditionsYield
In water; isopropyl alcohol at 40℃; Product distribution / selectivity;88%
In tert-butyl methyl ether; isopropyl alcohol at 25℃; for 2h; Product distribution / selectivity;84%
In water at 25℃; for 2h; Product distribution / selectivity;83%
In hexane; tert-butyl methyl ether; isopropyl alcohol at 20℃; for 2h;81.5%
3144-16-9

(1S)-10-camphorsulfonic acid

103129-82-4

amlodipine

S-(-)-amlodipine (1S)-(+)-10-camphorsulfonate

Conditions
ConditionsYield
In water; isopropyl alcohol at 40℃;88%
103129-82-4

amlodipine

(S)-amlodipine (+/-)-10-camsylate hydrate

Conditions
ConditionsYield
With water In isopropyl alcohol at 15 - 20℃; for 5h;87.4%
65-86-1

orotic acid

103129-82-4

amlodipine

1040924-28-4

S-(-)-amlodipine orotate

Conditions
ConditionsYield
In methanol at 25℃; for 2h; Product distribution / selectivity;85%
In water at 20 - 25℃; for 2h; Product distribution / selectivity;85%
35963-20-3

(R)-10-camphorsulfonic acid

103129-82-4

amlodipine

S-(-)-amlopidine (1R)-(-)-10-camsylate

Conditions
ConditionsYield
In tert-butyl methyl ether; isopropyl alcohol at 25℃; for 2h; Product distribution / selectivity;84%
In water at 25℃; for 2h; Product distribution / selectivity;83%
In water; isopropyl alcohol at 15 - 20℃;62.3%
18069-17-5

2-methylglutaric acid

103129-82-4

amlodipine

(S)-(-)-amlodipine hemi-2-methylglutarate salt

Conditions
ConditionsYield
In ethanol at 20℃; for 1h;84%
104-15-4

toluene-4-sulfonic acid

103129-82-4

amlodipine

S(-) amlodipine tosylate

Conditions
ConditionsYield
In ethanol; water82.88%
59-67-6

nicotinic acid

103129-82-4

amlodipine

675605-61-5

(S)-(-)-amlodipine nicotinate

Conditions
ConditionsYield
In Petroleum ether for 5h; Heating / reflux;79.3%
125995-03-1

atorvastatin lactone

103129-82-4

amlodipine

(S)-3-ethyl-5-methyl-2-{[2-({7-[(3-anilinocarbonyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoyl}amino)ethoxy]methyl}-4-(2-chlorophenyl)-6-methyl-1,4-dihydro-3,5-pyridinedicarboxylate

Conditions
ConditionsYield
In ethanol for 18h; Heating / reflux;64%
39637-74-6

(1S)-(-)-camphanic chloride

103129-82-4

amlodipine

143191-86-0

(-)-2-<<2-(camphanoylamino)ethoxy>methyl>-4-(2-chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridine

Conditions
ConditionsYield
With pyridine In dichloromethane for 2h; Ambient temperature; Yields of byproduct given;
Raw Materials
88150-42-9
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    103129-82-4

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Chemistry

Product Name: Levamlodipine besylate (CAS NO.103129-82-4)


Molecular Formula: C20H25N2O5Cl
Molecular Weight: 408.88g/mol
Index of Refraction: 1.546 
Molar Refractivity: 105.419 cm3 
Molar Volume: 333.02 cm3 
Surface Tension: 44.445 dyne/cm 
Density: 1.228 g/cm3 
Flash Point: 272.617 °C 
Enthalpy of Vaporization: 80.168 kJ/mol
Product Categories: Pharmaceutical material and intermeidates

Uses

 Levamlodipine besylate (CAS NO.103129-82-4) is mainly used as anti-cardiovascular drugs.

Analytical Methods

Quality standards and key quality indicators: WS1-(X-019)-2002Z

Specification

 Levamlodipine besylate (CAS NO.103129-82-4) is also named as (S)-Amlodipine;3,5-Pyridinedicarboxylic acid, 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (4S)- ; 3,5-Pyridinedicarboxylic acid, 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (S)- and so on.