Desloratadine supplier | CasNO.100643-71-8

Name
Desloratadine
EINECS 638-878-8
CAS No. 100643-71-8
Article Data43
CAS DataBase
Density 1.221 g/cm³
Solubility Freely soluble in methanol
Melting Point 150-151 °C
Formula C₁₉H₁₉ClN₂
Boiling Point 467.9 °C at 760 mmHg
Molecular Weight 310.826
Flash Point 236.8 °C
Transport Information
Appearance Beige solid
Safety
Risk Codes R11
Molecular Structure
Hazard Symbols
Synonyms Neoclarityn;Opulis;Sch 34117;5H-Benzo[5,6]cyclohepta[1,2-b]pyridine,8-chloro-6,11-dihydro-11-(4-piperidinylidene)-;8-Chloro-11-(4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;Aerius;Allex;Azomyr;Clarinex;Descarboethoxyloratadine;NSC675447;8-Chloro-6,11-dihydro-11-(4-piperdinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;
PSA 24.92000
LogP 4.34770

Synthetic route

: 79794-75-5
loratadine

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
In ethanol; water Reflux; Inert atmosphere; Alkaline conditions;	98.5%
With C22H40N4(2+)*2BF4(1-) In toluene at 80℃; for 0.666667h;	98.5%
With sodium hydroxide In ethanol; water at 100 - 105℃; for 5h; Concentration; Solvent; Time; Temperature; Autoclave; Inert atmosphere; Large scale;	96%

: 8-chloro-6,11-dihydro-11-(4-piperidinylydene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine carbon dioxide adduct

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Stage #1: 8-chloro-6,11-dihydro-11-(4-piperidinylydene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine carbon dioxide adduct In ethanol for 1h; Heating / reflux; Stage #2: In methanol; acetone Heating / reflux;	63%

: 32998-95-1
N-tert-butyl-3-methylpyridine-2-carboxamide

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) n-BuLi / 1.) THF, -40 deg C 2: POCl3 / Heating 3: 2.) aq. HCl / 1.) THF, reflux 4: CF3SO3H / Heating 5: Et3N / toluene / Heating 6: aq. KOH / Heating View Scheme

: 31255-57-9
3-[2-(3-chlorophenyl)ethyl]-2-pyridine-carbonitrile

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 2.) aq. HCl / 1.) THF, reflux 2: CF3SO3H / Heating 3: Et3N / toluene / Heating 4: aq. KOH / Heating View Scheme

: 107285-30-3
3-<2-(3-chlorophenyl)ethyl>-N-(1,1-dimethylethyl)-2-pyridinecarboxamide

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: POCl3 / Heating 2: 2.) aq. HCl / 1.) THF, reflux 3: CF3SO3H / Heating 4: Et3N / toluene / Heating 5: aq. KOH / Heating View Scheme

: 130642-50-1
{3-[2-(3-Chloro-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: CF3SO3H / Heating 2: Et3N / toluene / Heating 3: aq. KOH / Heating View Scheme

: 620-20-2
1-Chloro-3-chloromethyl-benzene

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) n-BuLi / 1.) THF, -40 deg C 2: POCl3 / Heating 3: 2.) aq. HCl / 1.) THF, reflux 4: CF3SO3H / Heating 5: Et3N / toluene / Heating 6: aq. KOH / Heating View Scheme

: 38092-89-6
N-methyldesloratadine

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / toluene / Heating 2: aq. KOH / Heating View Scheme
With potassium hydroxide In ethanol; water
With potassium hydroxide In ethanol; water
Multi-step reaction with 2 steps 1: triethylamine / toluene / 3 h / Reflux 2: potassium hydroxide / ethanol / 6 h / Reflux View Scheme

: 100643-73-0
8-chloro-6,11-dihydro-11-(1-cyano-4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
In hydrogenchloride; water; acetic acid	11.5 grams (93%)

: 8-Chloro-6,11-dihydro-11-(4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine acetic acid salt

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
With potassium carbonate; pyrographite In chloroform; water for 0.5h; pH=~ 10 - 12; Product distribution / selectivity;
Stage #1: 8-Chloro-6,11-dihydro-11-(4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine acetic acid salt With pyrographite In water at 20℃; for 1h; Stage #2: With potassium carbonate In water at 65 - 70℃; for 6 - 12h; pH=10 - 12; Product distribution / selectivity;

: 31251-41-9
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrahydrofuran / Reflux 2: sulfuric acid / 4.5 h / 20 °C 3: triethylamine / toluene / 3 h / Reflux 4: potassium hydroxide / ethanol / 6 h / Reflux View Scheme

: 63463-36-5
(1-methyl-4-piperidyl)magnesium chloride

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrahydrofuran / Reflux 2: sulfuric acid / 4.5 h / 20 °C 3: triethylamine / toluene / 3 h / Reflux 4: potassium hydroxide / ethanol / 6 h / Reflux View Scheme

: 38089-93-9
8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol

: 100643-71-8
descarboethoxyloratadine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 4.5 h / 20 °C 2: triethylamine / toluene / 3 h / Reflux 3: potassium hydroxide / ethanol / 6 h / Reflux View Scheme

: 100643-71-8
descarboethoxyloratadine

: 109-61-5
propoxycarbonyl chloride

: Propyl-4-(8-chlor-5,6-dihydro-11H-benzo-<5,6>-cyclohepta-<1,2-b>-pyridin-11-ylidin)-1-piperidincarboxylat

Conditions

Conditions	Yield
In toluene at 50℃; for 1h;	100%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h;

: 938-79-4
(2R)-2-phenylbutanoic acid

: 100643-71-8
descarboethoxyloratadine

: (R)-1-[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-2-phenyl-butan-1-one

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;	100%

: 100-28-7
4-Nitrophenyl isocyanate

: 100643-71-8
descarboethoxyloratadine

: 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-(4-nitrophenyl)piperidine-1-carboxamide

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	100%

: 100643-71-8
descarboethoxyloratadine

: 1609-86-5
Tert-butyl isocyanate

: N-(t-butyl)-4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxamide

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	100%

: 100643-71-8
descarboethoxyloratadine

: 103-71-9
phenyl isocyanate

: 169252-51-1
4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-phenylpiperidine-1-carboxamide

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	99%

: 100643-71-8
descarboethoxyloratadine

: 103-80-0
phenylacetyl chloride

: 1-(4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidin-1-yl)-2-phenylethan-1-one

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 7h;	98%
With pyridine In tetrahydrofuran for 48h; Ambient temperature;	36%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h;

: 124-38-9
carbon dioxide

: 100643-71-8
descarboethoxyloratadine

: 8-chloro-6,11-dihydro-11-(4-piperidinylydene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine carbon dioxide adduct

Conditions

Conditions	Yield
In acetone at 50℃; for 3h; Product distribution / selectivity; Heating / reflux;	97.5%
In methanol; acetone at 20 - 40℃; Product distribution / selectivity;	96%
In isopropyl alcohol; acetone at 20 - 40℃; Product distribution / selectivity;	95.2%
In ethanol; acetone at 20 - 45℃; for 0.5h; Product distribution / selectivity;	94.3%
In acetone; butan-1-ol at 20 - 40℃; Product distribution / selectivity;	94.3%

: 100643-71-8
descarboethoxyloratadine

: 121-51-7
3-nitrobenzenesulphonyl chloride

: 1423771-99-6
8-Chloro-11-(1-((3-nitrophenyl)sulfonyl)piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta-[1,2-b]pyridine

Conditions

Conditions	Yield
Stage #1: descarboethoxyloratadine With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: 3-nitrobenzenesulphonyl chloride In dichloromethane for 2h;	97%
With triethylamine In dichloromethane at 20℃; for 6h;	97.2%
With triethylamine In dichloromethane at 0℃; for 2h;

: 13205-48-6
4-(methylthio)benzoic acid

: 100643-71-8
descarboethoxyloratadine

: 169252-29-3
[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-(4-methylsulfanyl-phenyl)-methanone

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;	97%

: 529-64-6
Tropic acid

: 100643-71-8
descarboethoxyloratadine

: 169250-67-3
1-[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-3-hydroxy-2-phenyl-propan-1-one

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;	97%

: 100643-71-8
descarboethoxyloratadine

: 16588-74-2
3,5-ditrifluoromethylisocyanate

: N-(3,5-bis(trifluoromethyl)phenyl)-4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxamide

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	97%

: 100643-71-8
descarboethoxyloratadine

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 8-Chloro-11-(1-((4-nitrophenyl)sulfonyl)piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta-[1,2-b]pyridine

Conditions

Conditions	Yield
With pyridine at -5℃; for 12h;	96%
Stage #1: descarboethoxyloratadine With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: 4-Nitrobenzenesulfonyl chloride In dichloromethane for 2h;	88%
With potassium carbonate In toluene Ambient temperature;
With dmap In pyridine at 20℃;
With triethylamine In dichloromethane at 0℃; for 2h;

: 100643-71-8
descarboethoxyloratadine

: 5416-93-3
4-Methoxyphenyl isocyanate

: 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-(4-methoxyphenyl)piperidine-1-carboxamide

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	96%

: 3222-49-9
5-methylnicotinic acid

: 100643-71-8
descarboethoxyloratadine

: [4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-(5-methyl-pyridin-3-yl)-methanone

Conditions

Conditions	Yield
With boric acid In toluene Concentration; Reflux;	95%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 18h; Ambient temperature;	44%

: 100643-71-8
descarboethoxyloratadine

: 1129-28-8
3-methoxycarbonylbenzyl bromide

: methyl 3-[4-(8-chloro-5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidin-1-ylmethyl]benzoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	95%

: 100643-71-8
descarboethoxyloratadine

: 122-04-3
4-nitro-benzoyl chloride

: (4-(8-Chloro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(6H)-ylidene)piperidin-1-yl)(4-nitrophenyl)methanone

Conditions

Conditions	Yield
Stage #1: descarboethoxyloratadine With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: 4-nitro-benzoyl chloride In dichloromethane for 2h;	95%
With triethylamine In dichloromethane at 0℃; for 2h;

: 24424-99-5
di-tert-butyl dicarbonate

: 100643-71-8
descarboethoxyloratadine

: tert-butyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 5h;	94%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h;

: 1-bromo-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethane-1-sulfonyl fluoride

: 100643-71-8
descarboethoxyloratadine

: (E)-2-(4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidin-1-yl)ethene-1-sulfonyl fluoride

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃; stereoselective reaction;	94%

: 622-47-9
4-tolylacetic acid

: 100643-71-8
descarboethoxyloratadine

: 1-[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-2-p-tolyl-ethanone

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;	93%

: 621-36-3
m-methylphenylacetic acid

: 100643-71-8
descarboethoxyloratadine

: 1-[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-2-m-tolyl-ethanone

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;	93%

: 100643-71-8
descarboethoxyloratadine

: 1548-13-6
p-trifluoromethyl-phenylisocyanate

: 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-(4-(trifluoromethyl)phenyl)piperidine-1-carboxamide

Conditions

Conditions	Yield
In tetrahydrofuran at 20 - 23℃; for 6h;	93%

: 100643-71-8
descarboethoxyloratadine

: 157688-46-5
2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid

: t-butyl 4-(2-(4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidin-1-yl)-2-oxoethyl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 24h;	93%

: 124-38-9
carbon dioxide

: 100643-71-8
descarboethoxyloratadine

: 0.5CO2*C19H19ClN2

Conditions

Conditions	Yield
In ethanol; ethyl acetate at 5℃; for 2h; Product distribution / selectivity;	92.5%
In ethyl acetate for 0.5h;

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 100643-71-8
descarboethoxyloratadine

: (5-Bromo-pyridin-3-yl)-[4-(8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-methanone

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 18h; Ambient temperature;	92%

: C11H12NO4(1-)*K(1+)

: 100643-71-8
descarboethoxyloratadine

: C29H30ClN3O2

Conditions

Conditions	Yield
With manganese(IV) oxide; copper(l) iodide; zinc diacetate In N,N-dimethyl-formamide at 30℃; for 20h; Inert atmosphere; Sealed tube; chemoselective reaction;	92%

: 1591-95-3
pentafluorophenyl isocyanate

: 100643-71-8
descarboethoxyloratadine

: 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-(perfluorophenyl)piperidine-1-carboxamide

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	92%

: 100643-71-8
descarboethoxyloratadine

: 501-52-0
3-Phenylpropionic acid

: 1-[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-3-phenyl-propan-1-one

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;	91%

: 102-32-9
3,4-dihydroxyphenylacetate

: 100643-71-8
descarboethoxyloratadine

: 1-[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-2-(3,4-dihydroxy-phenyl)-ethanone

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;	90.3%

: 7782-37-8
erythro-2-phenyl-3-methylpentanoic acid

: 100643-71-8
descarboethoxyloratadine

: 1-[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-3-methyl-2-phenyl-pentan-1-one

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;	90%

Desloratadine Chemical Properties

Molecular Structure of Desloratadine (CAS NO.100643-71-8):

Systematic Name: 8-Chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
Molecular Weight: 310.82056 [g/mol]
Molecular Formula: C₁₉H₁₉ClN₂
XLogP3: 4.5
H-Bond Donor: 1
H-Bond Acceptor: 2
Appearance: Beige Solid
Melting Point: 150-151 °C
storage temp.: 2-8 °C
Index of Refraction: 1.625
Molar Refractivity: 90.05 cm³
Molar Volume: 254.3 cm³
Surface Tension: 50 dyne/cm
Density: 1.221 g/cm³
Flash Point: 236.8 °C
Enthalpy of Vaporization: 73 kJ/mol
Boiling Point: 467.9 °C at 760 mmHg
Vapour Pressure: 6.25E-09 mmHg at 25 °C
Classification Code: Anti-allergic agents; Antihistamine; Antihistaminic; Cholinergic Agents; Cholinergic Antagonists; Histamine Agents; Histamine Antagonists; Histamine H1 Antagonists, Non-Sedating; Histamine H1 antagonists; Neurotransmitter Agents; Treatment of seasonal allergic rhinitis [H1 receptor antagonist]
Product Categories: Active Pharmaceutical Ingredients; Antihistaminic; Various Metabolites and Impurities; Intermediates & Fine Chemicals; Metabolites; Pharmaceuticals

Desloratadine Uses

Desloratadine (CAS NO.100643-71-8) is used as respiratory and anti-allergic drug to treat allergies and also can be as tablets and syrup to treat and release allergies.

Desloratadine Specification

Desloratadine (CAS NO.100643-71-8), its Synonyms are 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridine ; Aerius ; Azomyr ; Clarinex ; Denosin ; Neoclarityn ; 5H-Benzo(5,6)cyclohepta(1,2-b)pyridine, 8-chloro-6,11-dihydro-11-(4-piperidinylidene)- .

Product Name

Desloratadine

Synthetic route

Desloratadine Chemical Properties

Desloratadine Uses

Desloratadine Specification

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