Product Name

  • Name

    [4-(4-Amino-6,7-dimethoxy-quinazolin-2- yl)piperazin-1-yl]-(2,5-dioxabi cyclo[4.4.0]deca-6,8,10-trien-4-yl)methanone

  • EINECS
  • CAS No. 74191-85-8
  • Article Data9
  • CAS DataBase
  • Density 1.371 g/cm3
  • Solubility
  • Melting Point 289-290 °C
  • Formula C23H25N5O5
  • Boiling Point 718 °C at 760 mmHg
  • Molecular Weight 451.482
  • Flash Point 388 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes R23/24/25; R34; R40; R43; R36/37/38; R38
  • Molecular Structure Molecular Structure of 74191-85-8 ([4-(4-Amino-6,7-dimethoxy-quinazolin-2- yl)piperazin-1-yl]-(2,5-dioxabi cyclo[4.4.0]deca-6,8,10-trien-4-yl)methanone)
  • Hazard Symbols T,Xi
  • Synonyms Piperazine,1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]-(9CI);[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl](2,3-dihydro-1,4-benzodioxin-2-yl)methanone;Doxazosine;UK 33274;piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]-;2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)pipérazin-1-yl]-6,7-diméthoxyquinazolin-4-amine;
  • PSA 175.02000
  • LogP 2.88670

Synthetic route

2-chloro-6,7-dimethoxyquinazolin-4-amine
23680-84-4

2-chloro-6,7-dimethoxyquinazolin-4-amine

(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone
70918-00-2

(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
In butan-1-ol Reflux;88%
In butan-1-ol for 5h; Heating;83%
1,4-benzodioxane-2-carboxylic acid
3663-80-7, 34385-93-8, 70918-53-5, 70918-54-6

1,4-benzodioxane-2-carboxylic acid

4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline
60547-97-9

4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 5.16667h;80%
ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate
4739-94-0

ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / 6 h / 70 - 80 °C
2: 83 percent / butan-1-ol / 5 h / Heating
View Scheme
benzene-1,2-diol
120-80-9

benzene-1,2-diol

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / potassium hydroxide; polyethylene glycol-400; potassium carbonate / toluene / 3.75 h / Heating
2: 65 percent / 6 h / 70 - 80 °C
3: 83 percent / butan-1-ol / 5 h / Heating
View Scheme
(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(1H-imidazol-1-yl)methanone
1246188-97-5

(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(1H-imidazol-1-yl)methanone

4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline
60547-97-9

4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
In tetrahydrofuran at 25 - 28℃; Product distribution / selectivity;
1,4-benzodioxane-2-carboxylic acid
3663-80-7, 34385-93-8, 70918-53-5, 70918-54-6

1,4-benzodioxane-2-carboxylic acid

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 2 h / 20 - 25 °C
2: tetrahydrofuran / 25 - 28 °C
View Scheme
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere
2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C
3: butan-1-ol / Reflux
View Scheme
2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin
3663-82-9

2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide; potassium permanganate / water / 0 °C
2: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: potassium hydroxide; potassium permanganate / water / 0 °C
2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C
4: butan-1-ol / Reflux
View Scheme
2-Iodophenol
533-58-4

2-Iodophenol

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium carbonate / N,N-dimethyl-formamide; water; ethyl acetate / 24 h / 50 °C
2: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C
3: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
4: potassium hydroxide; potassium permanganate / water / 0 °C
5: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C
View Scheme
Multi-step reaction with 7 steps
1: potassium carbonate / N,N-dimethyl-formamide; water; ethyl acetate / 24 h / 50 °C
2: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C
3: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
4: potassium hydroxide; potassium permanganate / water / 0 °C
5: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere
6: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C
7: butan-1-ol / Reflux
View Scheme
C13H15IO5

C13H15IO5

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C
2: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
3: potassium hydroxide; potassium permanganate / water / 0 °C
4: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C
2: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
3: potassium hydroxide; potassium permanganate / water / 0 °C
4: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere
5: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C
6: butan-1-ol / Reflux
View Scheme
2-(2-iodophenoxy)propane-1,3-diol

2-(2-iodophenoxy)propane-1,3-diol

doxazosin
74191-85-8

doxazosin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
2: potassium hydroxide; potassium permanganate / water / 0 °C
3: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
2: potassium hydroxide; potassium permanganate / water / 0 °C
3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere
4: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C
5: butan-1-ol / Reflux
View Scheme
acetyl chloride
75-36-5

acetyl chloride

doxazosin
74191-85-8

doxazosin

N-(2-(4-(2,3-dihydrobenzo[b][1,4]dioxine-2-carbonyl)piperazin-1-yl)-6,7-dimethoxyquinazolin-4-yl)acetamide

N-(2-(4-(2,3-dihydrobenzo[b][1,4]dioxine-2-carbonyl)piperazin-1-yl)-6,7-dimethoxyquinazolin-4-yl)acetamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide36%
methanesulfonic acid
75-75-2

methanesulfonic acid

doxazosin
74191-85-8

doxazosin

doxazosin mesylate

doxazosin mesylate

Conditions
ConditionsYield
In acetone at 25 - 38℃;
methanesulfonic acid
75-75-2

methanesulfonic acid

doxazosin
74191-85-8

doxazosin

doxazosin mesylate

doxazosin mesylate

Conditions
ConditionsYield
In acetone at 10 - 25℃;
doxazosin
74191-85-8

doxazosin

doxazosin hydrochloride

doxazosin hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 10 - 25℃; pH=2 - 3;
doxazosin
74191-85-8

doxazosin

C23H24N4O6

C23H24N4O6

Conditions
ConditionsYield
With sodium dodecyl-sulfate; sodium hydrogensulfite In ethanol; water Solvent; Reagent/catalyst; Reflux;

Doxazosin Specification

The Doxazosin, with the CAS registry number 74191-85-8, has the systematic name of [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl](2,3-dihydro-1,4-benzodioxin-2-yl)methanone. Its classification codes are: Adrenergic Agents; Adrenergic Antagonists; Adrenergic alpha-antagonists; Antihypertensive agents; Cardiovascular Agents; Neurotransmitter Agents. The molecular formula of this chemical is C23H25N5O5.

The physical properties of Doxazosin are as following: (1)ACD/LogP: 0.65; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.33; (4)ACD/LogD (pH 7.4): 0.6; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1.65; (7)ACD/KOC (pH 5.5): 5.62; (8)ACD/KOC (pH 7.4): 48.37; (9)#H bond acceptors: 10; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 89.49 Å2; (13)Index of Refraction: 1.657; (14)Molar Refractivity: 121.23 cm3; (15)Molar Volume: 329.2 cm3; (16)Polarizability: 48.06×10-24cm3; (17)Surface Tension: 64.9 dyne/cm; (18)Density: 1.371 g/cm3; (19)Flash Point: 388 °C; (20)Enthalpy of Vaporization: 104.92 kJ/mol; (21)Boiling Point: 718 °C at 760 mmHg; (22)Vapour Pressure: 1.83E-20 mmHg at 25°C.

Preparation of Doxazosin: It can be prepared by 4-Amino-2-chloro-6,7 -dimethoxy-quinazoline and 2-(1-carboxymethyl piperazine carbonyl)-1,4-Benzodioxan.

Doxazosin can be prepared by 4-Amino-2-chloro-6,7 -dimethoxy-quinazoline and 2-(1-carboxymethyl piperazine carbonyl)-1,4-Benzodioxan

Uses of Doxazosin: It is used to treat high blood pressure and urinary retention associated with benign prostatic hyperplasia. It is a kind of alpha-1 adrenergic receptor blocker that inhibits the binding of norepinephrine to the alpha-1 receptors on the membrane of vascular smooth muscle cells. And this primary effect of the inhibition is relaxed vascular smooth muscle tone, which decreases peripheral vascular resistance, leading to decreased blood pressure.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4Oc5c(OC4)cccc5
(2)InChI: InChI=1/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
(3)InChIKey: RUZYUOTYCVRMRZ-UHFFFAOYAW

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View