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79794-75-5

Basic Information
CAS No.: 79794-75-5
Name: Loratadine
Article Data: 28
Molecular Structure:
Molecular Structure of 79794-75-5 (Loratadine)
Formula: C22H23ClN2O2
Molecular Weight: 382.89
Synonyms: Sch 29851;Bedix Loratadina;Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylate;Claratyne;Biloina;Histaloran;Lorastine;Alarin;Loratadine (JAN/USAN);Loratadina [Spanish];Loradif;Claritin D;Sensibit;Loranox;1-Piperidinecarboxylic acid, 4-(8-chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-, ethyl ester;Sohotin;Clarityne;Fristamin;Bonalerg;Aerotina;Claritin;Rhinase;Alerpriv;Lertamine;Allertidin;Loratadine (79794-75-5);Loratadina;Clarityne-D;Lorantis;Pylor;Lowadina;Lesidas;Loratyne;Tadine;
EINECS: 1308068-626-2
Density: 1.261 g/cm3
Melting Point: 134-136 ºC
Boiling Point: 531.3 ºC at 760 mmHg
Flash Point: 275.1 ºC
Solubility: DMSO: 26 mg/mL, soluble
Appearance: white crystalline solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25
PSA: 42.43000
LogP: 4.82570
Synthetic route
541-41-3

chloroformic acid ethyl ester

38092-89-6

N-methyldesloratadine

79794-75-5

loratadine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In toluene at 60 - 75℃; for 1 - 2h;90%
Stage #1: chloroformic acid ethyl ester; N-methyldesloratadine With N-ethyl-N,N-diisopropylamine In toluene at 60 - 75℃; for 1 - 2h;
Stage #2: With hydrogenchloride In water; toluene
73%
With triethylamine In toluene for 3h; Reflux;72%
216870-24-5

diethyl N-ethoxycarbonylpiperidine-4-phosphonate

79794-75-5

loratadine

Conditions
ConditionsYield
With hydrogenchloride In N,N-dimethyl acetamide; isopropyl alcohol at 20 - 140℃; under 760.051 Torr; for 2h;82%
20970-75-6

2-cyano-3-methylpyridine

79794-75-5

loratadine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 97 percent / conc. H2SO4 / 0.5 h / 75 °C
2: 1.) n-BuLi, NaBr / 1.) THF, hexane, -40 deg C, 10 min, 2.) THF, hexane, -40 deg C, 30 min
3: 1.) POCl3, 2.) 50percent aq. NaOH / 1.) reflux, 3 h, 2.) 30 deg C, 2 h, pH 8
4: tetrahydrofuran / 0.5 h / 40 - 50 °C
5: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
6: 20 g / BF3 / 4 h / 120 °C
7: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 7 steps
1: 97 percent / conc. H2SO4 / 0.5 h / 75 °C
2: 1.) n-BuLi, NaBr / 1.) THF, hexane, -40 deg C, 10 min, 2.) THF, hexane, -40 deg C, 30 min
3: 1.) POCl3, 2.) 50percent aq. NaOH / 1.) reflux, 3 h, 2.) 30 deg C, 2 h, pH 8
4: tetrahydrofuran / 0.5 h / 40 - 50 °C
5: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
6: 91 percent / hydrofluoric acid, BF3 / -35 °C
7: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 7 steps
1: 97 percent / conc. H2SO4 / 0.5 h / 75 °C
2: 1.) n-BuLi, NaBr / 1.) THF, hexane, -40 deg C, 10 min, 2.) THF, hexane, -40 deg C, 30 min
3: 1.) POCl3, 2.) 50percent aq. NaOH / 1.) reflux, 3 h, 2.) 30 deg C, 2 h, pH 8
4: tetrahydrofuran / 0.5 h / 40 - 50 °C
5: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
6: 44 percent / polyphosphoric acid (PPA) / 8 h / 190 °C
7: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sulfuric acid / 0.5 h / 70 - 75 °C
2.1: n-butyllithium / tetrahydrofuran / 0.33 h / -30 - -10 °C / Inert atmosphere
2.2: 1 h / -10 °C / Inert atmosphere
3.1: trichlorophosphate / 4 h / 110 °C
4.1: magnesium; iodine / tetrahydrofuran; ethylene dibromide / 1 h / 75 °C / Inert atmosphere
4.2: 1 h / 40 - 50 °C / Inert atmosphere
4.3: 1 h / 20 °C / pH < 2 / Inert atmosphere
5.1: boric acid; sulfuric acid / chlorobenzene / 30 h / 80 - 90 °C
6.1: triethylamine / toluene / 2 h / 80 - 85 °C
View Scheme
32998-95-1

N-tert-butyl-3-methylpyridine-2-carboxamide

79794-75-5

loratadine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) n-BuLi, NaBr / 1.) THF, hexane, -40 deg C, 10 min, 2.) THF, hexane, -40 deg C, 30 min
2: 1.) POCl3, 2.) 50percent aq. NaOH / 1.) reflux, 3 h, 2.) 30 deg C, 2 h, pH 8
3: tetrahydrofuran / 0.5 h / 40 - 50 °C
4: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
5: 20 g / BF3 / 4 h / 120 °C
6: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 6 steps
1: 1.) n-BuLi, NaBr / 1.) THF, hexane, -40 deg C, 10 min, 2.) THF, hexane, -40 deg C, 30 min
2: 1.) POCl3, 2.) 50percent aq. NaOH / 1.) reflux, 3 h, 2.) 30 deg C, 2 h, pH 8
3: tetrahydrofuran / 0.5 h / 40 - 50 °C
4: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
5: 91 percent / hydrofluoric acid, BF3 / -35 °C
6: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 6 steps
1: 1.) n-BuLi, NaBr / 1.) THF, hexane, -40 deg C, 10 min, 2.) THF, hexane, -40 deg C, 30 min
2: 1.) POCl3, 2.) 50percent aq. NaOH / 1.) reflux, 3 h, 2.) 30 deg C, 2 h, pH 8
3: tetrahydrofuran / 0.5 h / 40 - 50 °C
4: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
5: 44 percent / polyphosphoric acid (PPA) / 8 h / 190 °C
6: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 5 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
View Scheme
Multi-step reaction with 5 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -30 - -10 °C / Inert atmosphere
1.2: 1 h / -10 °C / Inert atmosphere
2.1: trichlorophosphate / 4 h / 110 °C
3.1: magnesium; iodine / tetrahydrofuran; ethylene dibromide / 1 h / 75 °C / Inert atmosphere
3.2: 1 h / 40 - 50 °C / Inert atmosphere
3.3: 1 h / 20 °C / pH < 2 / Inert atmosphere
4.1: boric acid; sulfuric acid / chlorobenzene / 30 h / 80 - 90 °C
5.1: triethylamine / toluene / 2 h / 80 - 85 °C
View Scheme
31255-57-9

3-[2-(3-chlorophenyl)ethyl]-2-pyridine-carbonitrile

79794-75-5

loratadine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrofuran / 0.5 h / 40 - 50 °C
2: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
3: 20 g / BF3 / 4 h / 120 °C
4: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrahydrofuran / 0.5 h / 40 - 50 °C
2: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
3: 91 percent / hydrofluoric acid, BF3 / -35 °C
4: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrahydrofuran / 0.5 h / 40 - 50 °C
2: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
3: 44 percent / polyphosphoric acid (PPA) / 8 h / 190 °C
4: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: 2.) aq. HCl / 1.) THF, reflux
2: CF3SO3H / Heating
3: Et3N / toluene / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: magnesium; iodine / tetrahydrofuran; ethylene dibromide / 1 h / 75 °C / Inert atmosphere
1.2: 1 h / 40 - 50 °C / Inert atmosphere
1.3: 1 h / 20 °C / pH < 2 / Inert atmosphere
2.1: boric acid; sulfuric acid / chlorobenzene / 30 h / 80 - 90 °C
3.1: triethylamine / toluene / 2 h / 80 - 85 °C
View Scheme
107285-30-3

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

79794-75-5

loratadine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) POCl3, 2.) 50percent aq. NaOH / 1.) reflux, 3 h, 2.) 30 deg C, 2 h, pH 8
2: tetrahydrofuran / 0.5 h / 40 - 50 °C
3: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
4: 20 g / BF3 / 4 h / 120 °C
5: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 5 steps
1: 1.) POCl3, 2.) 50percent aq. NaOH / 1.) reflux, 3 h, 2.) 30 deg C, 2 h, pH 8
2: tetrahydrofuran / 0.5 h / 40 - 50 °C
3: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
4: 91 percent / hydrofluoric acid, BF3 / -35 °C
5: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 5 steps
1: 1.) POCl3, 2.) 50percent aq. NaOH / 1.) reflux, 3 h, 2.) 30 deg C, 2 h, pH 8
2: tetrahydrofuran / 0.5 h / 40 - 50 °C
3: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
4: 44 percent / polyphosphoric acid (PPA) / 8 h / 190 °C
5: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1: POCl3 / Heating
2: 2.) aq. HCl / 1.) THF, reflux
3: CF3SO3H / Heating
4: Et3N / toluene / Heating
View Scheme
Multi-step reaction with 4 steps
1.1: trichlorophosphate / 4 h / 110 °C
2.1: magnesium; iodine / tetrahydrofuran; ethylene dibromide / 1 h / 75 °C / Inert atmosphere
2.2: 1 h / 40 - 50 °C / Inert atmosphere
2.3: 1 h / 20 °C / pH < 2 / Inert atmosphere
3.1: boric acid; sulfuric acid / chlorobenzene / 30 h / 80 - 90 °C
4.1: triethylamine / toluene / 2 h / 80 - 85 °C
View Scheme
63463-36-5

(1-methyl-4-piperidyl)magnesium chloride

79794-75-5

loratadine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrofuran / 0.5 h / 40 - 50 °C
2: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
3: 20 g / BF3 / 4 h / 120 °C
4: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrahydrofuran / 0.5 h / 40 - 50 °C
2: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
3: 91 percent / hydrofluoric acid, BF3 / -35 °C
4: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrahydrofuran / 0.5 h / 40 - 50 °C
2: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
3: 44 percent / polyphosphoric acid (PPA) / 8 h / 190 °C
4: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: tetrahydrofuran / Reflux
2: sulfuric acid / 4.5 h / 20 °C
3: triethylamine / toluene / 3 h / Reflux
View Scheme

C-{3-[2-(3-Chloro-phenyl)-ethyl]-pyridin-2-yl}-C-(1-methyl-piperidin-4-yl)-methyleneamine

79794-75-5

loratadine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
2: 20 g / BF3 / 4 h / 120 °C
3: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
2: 91 percent / hydrofluoric acid, BF3 / -35 °C
3: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: 2 N aq. HCl / tetrahydrofuran / 1 h / 25 - 30 °C
2: 44 percent / polyphosphoric acid (PPA) / 8 h / 190 °C
3: 42.4 g / toluene / 1 h / 80 °C
View Scheme
119770-60-4

1-(METHYL-4-PIPERIDINYL)[3-(2-(3-CHLORO-PHENYL)ETHYL)-2-PYRIDINYL]METHANONE HYDROCHLORIDE

79794-75-5

loratadine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 20 g / BF3 / 4 h / 120 °C
2: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: 91 percent / hydrofluoric acid, BF3 / -35 °C
2: 42.4 g / toluene / 1 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: 44 percent / polyphosphoric acid (PPA) / 8 h / 190 °C
2: 42.4 g / toluene / 1 h / 80 °C
View Scheme
130642-50-1

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

79794-75-5

loratadine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CF3SO3H / Heating
2: Et3N / toluene / Heating
View Scheme
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Chemistry

Molecular structure:

Formula :C22H23ClN2O2 
Mol. mass: 382.88 g/mol 
Nominal Mass: 382 Da
Average Mass: 382.8832 Da
Monoisotopic Mass: 382.144806 Da 
Index of Refraction: 1.614
Molar Refractivity: 105.85 cm3
Molar Volume: 303.5 cm3
Surface Tension: 53.3 dyne/cm
Density: 1.261 g/cm3
Flash Point: 275.1 °C
Enthalpy of Vaporization: 80.68 kJ/mol
Boiling Point: 531.3 °C at 760 mmHg 
Melting Point: 134-136°C
Vapour Pressure: 2.26E-11 mmHg at 25°C
Storage temp: 2-8°C
Solubility DMSO: 26 mg/mL, soluble 
Appearance: White Crystalline Solid
InChI=1/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3
Smiles
C1(\c2c(cc(Cl)cc2)CCc2c1nccc2)=C1\CCN(C(OCC)=O)CC1
IUPAC name : Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidine)-1-piperidinecarboxylate  
Synonyms of Loratadine (CAS NO.79794-75-5):  Loratadine ; Loratadine-d5 ; Loratidine ; Claratyne ; Claritin ; Ethyl 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate ; 4(8-Chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate ; 4-(8-Chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl ester   
Product Categories: Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;API's;Histamine receptor

History

 Loratadine (CAS NO.79794-75-5) was eventually approved by the FDA.

Uses

 Loratadine (CAS NO.79794-75-5) is an antihistamine drug used to treat allergies.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements of Loratadine (CAS NO.79794-75-5): 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26 
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes. 
S36: Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Specification

 Loratadine (CAS NO.79794-75-5) is combined with pseudoephedrine, a decongestant; this makes it somewhat useful for colds as well as allergies, but adds potential side-effects of insomnia, nervousness and anxiety.
In the U.S. and UK, loratadine is the only drug of its class available over the counter (though it is no longer the only second generation antihistamine available in this manner).