• Name

  Vardenafil hydrochloride trihydrate

• EINECS 200-835-2
• CAS No. 224785-90-4
• Article Data12
• CAS DataBase
• Density 1.37 g/cm³
• Solubility Soluble in water and alcohol
• Melting Point 230-235 °C
• Formula C₂₃H₃₂N₆O₄S
• Boiling Point 692.2 °C at 760 mmHg
• Molecular Weight 488.611
• Flash Point 372.5 °C
• Transport Information
• Appearance White crystalline powder
• Safety 16-36/37
• Risk Codes 11-20/21/22-36
• Molecular Structure
• Hazard Symbols F,Xn
• Synonyms Piperazine,1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethyl-(9CI);2-[2-Ethoxy-5-(4-ethylpiperazin-1-yl-1-sulfonyl)phenyl]-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one;Nuviva;BAY 38-9456;1-((3-(3,4-Dihydro-5-methyl-4-oxo-7-propylimidazo(5,1-f)-as-triazin-2-yl)-4-ethoxyphenyl)sulfonyl)-4-ethylpiperazine;Vivanza;
• PSA 121.28000
• LogP 4.63100

Synthetic route

5308-25-8

4-ethylpiperazine

224789-21-3

2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

224785-90-4

vardenafil

Conditions

Conditions	Yield
Stage #1: 2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one With chlorosulfonic acid at 0 - 22℃; for 0.75h; Stage #2: 4-ethylpiperazine In dichloromethane at -3 - 25℃; for 0.75h; Product distribution / selectivity;

5308-25-8

4-ethylpiperazine

224789-26-8

4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)-benzenelsulfonic acid chloride

224785-90-4

vardenafil

Conditions

Conditions	Yield
In dichloromethane

224789-21-3

2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

224785-90-4

vardenafil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorosulfonic acid / dichloromethane / 24 h / 23 - 90 °C 2: dichloromethane View Scheme

5308-25-8

4-ethylpiperazine

224789-21-3

2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

224785-90-4

vardenafil

Conditions

Conditions	Yield
Stage #1: 2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one With chlorosulfonic acid at 0 - 22℃; for 0.75h; Stage #2: 4-ethylpiperazine In dichloromethane at -3 - 25℃; for 0.75h; Product distribution / selectivity;

224789-21-3

2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

224785-90-4

vardenafil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorosulfonic acid / dichloromethane / 24 h / 23 - 90 °C 2: dichloromethane View Scheme

5308-25-8

4-ethylpiperazine

224789-26-8

4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)-benzenelsulfonic acid chloride

224785-90-4

vardenafil

Conditions

Conditions	Yield
In dichloromethane

224785-90-4

vardenafil

vardenafil hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 50℃; Solvent; Temperature; pH-value; Reagent/catalyst;	77%

224785-90-4

vardenafil

1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate

Conditions

Conditions	Yield
With hydrogenchloride; water In acetone at 29 - 55℃; for 0.5h;

1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate

224785-90-4

vardenafil

1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride monohydrate

Conditions

Conditions	Yield
Stage #1: vardenafil With water In acetone at 28℃; for 0.166667h; Stage #2: With hydrogenchloride; water In acetone at 5 - 55℃; for 0.5h; Stage #3: 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate In acetone at 3℃;

1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate

224785-90-4

vardenafil

1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride trihydrate

Conditions

Conditions	Yield
Stage #1: vardenafil With hydrogenchloride; water In acetone at 5 - 56℃; for 0.5h; Stage #2: 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate In acetone at 3℃;

18162-48-6

tert-butyldimethylsilyl chloride

224785-90-4

vardenafil

C29H46N6O4SSi

Conditions

Conditions	Yield
In N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide; acetonitrile at 70℃; for 0.5h;

Vardenafil hydrochloride trihydrate Chemical Properties

Vardenafil hydrochloride trihydrate Uses