Loratadine supplier | CasNO.79794-75-5

Name
Loratadine
EINECS 1308068-626-2
CAS No. 79794-75-5
Article Data28
CAS DataBase
Density 1.261 g/cm³
Solubility DMSO: 26 mg/mL, soluble
Melting Point 134-136 ºC
Formula C₂₂H₂₃ClN₂O₂
Boiling Point 531.3 ºC at 760 mmHg
Molecular Weight 382.89
Flash Point 275.1 ºC
Transport Information
Appearance white crystalline solid
Safety 22-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

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

: 79794-75-5
loratadine

Conditions

Conditions	Yield
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

: 541-41-3
chloroformic acid ethyl ester

: 7087-68-5
N-ethyl-N,N-diisopropylamine

: 38092-89-6
N-methyldesloratadine

: 79794-75-5
loratadine

Conditions

Conditions	Yield
In toluene; acetonitrile	42.4 g (HPLC purity 97.4%)
In toluene; acetonitrile	42.4 g (HPLC purity 97.4%)

...Expand

: 541-41-3
chloroformic acid ethyl ester

: 7440-44-0
pyrographite

: 38092-89-6
N-methyldesloratadine

: 79794-75-5
loratadine

Conditions

Conditions	Yield
In toluene; acetonitrile

...Expand

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

: 79794-75-5
loratadine

Conditions

Conditions	Yield
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

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

: 79794-75-5
loratadine

Conditions

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

: 100643-71-8
descarboethoxyloratadine

: 1609-47-8
diethyl dicarbonate

: 79794-75-5
loratadine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h;

: 5570-77-4
4-chloro-1-methylpiperidine

: 79794-75-5
loratadine

Conditions

Conditions	Yield
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

: 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%

: 3731-53-1
4-(aminomethyl)pyridine

: 79794-75-5
loratadine

: ethyl 4-(8-((pyridin-4-ylmethyl)amino)-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
With C47H70BrO4PPdSi; sodium t-butanolate In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Inert atmosphere; Sealed tube;	98%

: 79794-75-5
loratadine

: potassium vinyltrifluoroborate

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

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; water at 90℃; for 2h; Schlenk technique; Inert atmosphere;	91%

: 5764-82-9
bromo(2-ethoxy-2-oxoethyl)zinc

: 79794-75-5
loratadine

: ethyl 4-[13-(2-ethoxy-2-oxoethyl)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]piperidine-1-carboxylate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N,N,N,N,-tetramethylethylenediamine; C38H62P2 In tetrahydrofuran at 20℃; for 16h; Negishi Coupling; Inert atmosphere;	90%

: 358-23-6
trifluoromethylsulfonic anhydride

: 79794-75-5
loratadine

: 603-35-0
triphenylphosphine

: (8-Chloro-11-(1-(ethoxycarbonyl)piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-4-yl)triphenylphosphonium trifluoromethanesulfonate

Conditions

Conditions	Yield
Stage #1: trifluoromethylsulfonic anhydride; loratadine at -78℃; Inert atmosphere; Stage #2: triphenylphosphine Inert atmosphere; Cooling; Stage #3: Alkaline conditions; Inert atmosphere; regioselective reaction;	88%
at -78 - 20℃; Alkaline conditions;	88%
Stage #1: trifluoromethylsulfonic anhydride; loratadine In dichloromethane at -78℃; Inert atmosphere; Stage #2: triphenylphosphine In dichloromethane at -78 - 20℃; Inert atmosphere; regioselective reaction;

...Expand

: 79794-75-5
loratadine

: ethyl 4-[8-hydroxy-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene]-1-piperidine carboxylate

Conditions

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 14h; Schlenk technique; Inert atmosphere;	87%

: 79794-75-5
loratadine

isopropyl halide: isopropyl halide

: C25H29ClN2O2

Conditions

Conditions	Yield
With tris-(trimethylsilyl)silane; [Ir[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine]2(4,4′-di-t-Bu-2,2′-bipyridine)]PF6; oxygen; trifluoroacetic acid In acetone at 20℃; for 24h; Minisci Aromatic Substitution; Irradiation; regioselective reaction;	83%

: 79794-75-5
loratadine

: 73183-34-3
bis(pinacol)diborane

: ethyl 4-(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-11Hbenzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
With potassium acetate; palladium diacetate; XPhos In 1,4-dioxane at 80℃; for 10h; Schlenk technique;	83%
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos In 1,4-dioxane at 110℃; for 12h; Inert atmosphere; Sealed tube;	705.4 mg

: 450-95-3
2-fluoroacetophenone

: 79794-75-5
loratadine

: (1-fluoro-2-oxo-2-phenylethyl)claritin

Conditions

Conditions	Yield
With chloro[(di(1-adamantyl)-N-butylphosphine)-2-(2-aminobiphenyl)]palladium(II); caesium carbonate In toluene at 100℃; for 14h; Schlenk technique; Inert atmosphere;	82%

: 358-23-6
trifluoromethylsulfonic anhydride

: 5-(diphenylphosphaneyl)-2-(trifluoromethyl)pyridine

: 79794-75-5
loratadine

: (8-chloro-11-(1-(ethoxycarbonyl)piperidin-4-ylidene)-6,11-dihydro-5Hbenzo[5,6]cyclohepta[1,2-b]pyridin-4-yl)diphenyl(6-(trifluoromethyl)pyridin-3-yl)phosphonium trifluoromethanesulfonate

Conditions

Conditions	Yield
Stage #1: trifluoromethylsulfonic anhydride; 5-(diphenylphosphaneyl)-2-(trifluoromethyl)pyridine; loratadine In dichloromethane at -50℃; for 1h; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -78 - 20℃; for 0.333333 - 0.5h; Inert atmosphere;	81%

...Expand

: 646-06-0
1,3-DIOXOLANE

: 79794-75-5
loratadine

A: ethyl 4-(8-formyl-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

B: ethyl 4-(8-(1,3-dioxolan-4-yl)-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 1,3-DIOXOLANE; loratadine With potassium phosphate; (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine for 0.166667h; Glovebox; Stage #2: With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate at 23℃; for 72h; Sealed tube; Irradiation; Stage #3: With hydrogenchloride In water; acetone at 23℃;	A 78% B n/a

Yield

Stage #1: 1,3-DIOXOLANE; loratadine With potassium phosphate; (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine for 0.166667h; Glovebox;
Stage #2: With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate at 23℃; for 72h; Sealed tube; Irradiation;
Stage #3: With hydrogenchloride In water; acetone at 23℃;

A 78%
B n/a

...Expand

: 79794-75-5
loratadine

: 17997-47-6
2-tri-n-butylstannylpyridine

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

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); cesium fluoride; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;	78%

: 358-23-6
trifluoromethylsulfonic anhydride

: 4-(diphenylphosphaneyl)-2,6-dimethylpyridine

: 79794-75-5
loratadine

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

Conditions

Conditions	Yield
Stage #1: trifluoromethylsulfonic anhydride; loratadine In dichloromethane at -78℃; for 0.583333h; Inert atmosphere; Stage #2: 4-(diphenylphosphaneyl)-2,6-dimethylpyridine In dichloromethane at -50℃; for 0.5h; Inert atmosphere; Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -78 - 20℃; Inert atmosphere;	78%

...Expand

: 75-88-7
1,1,1-trifluoro-2-chloroethane

: 79794-75-5
loratadine

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

Conditions

Conditions	Yield
With 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; nickel dibromide; zinc In N,N-dimethyl acetamide at 80℃; for 12h; Inert atmosphere; Schlenk technique;	78%

: 2-(allylsulfonyl)-5-(trifluoromethyl)pyridine

: 79794-75-5
loratadine

: ethyl 4-(8-(5-(trifluoromethyl)pyridin-2-yl)-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 18h; Inert atmosphere;	77%

: 79794-75-5
loratadine

A: 4-(8-Chloro-7-nitro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidine-1-carboxylic acid ethyl ester

B: 4-(8-Chloro-9-nitro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidine-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With sulfuric acid; potassium nitrate at -5℃; for 16h;	A 12% B 76%

: 124-38-9
carbon dioxide

: 79794-75-5
loratadine

: 143540-41-4
8-cyano-11-(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Conditions

Conditions	Yield
With nickel(II) acetylacetonate; potassium fluoride; phenylsilane; ammonia; zinc; bis(2-diphenylphosphinoethyl)phenylphosphine In 1-methyl-pyrrolidin-2-one at 90 - 140℃; under 760.051 Torr; for 20h; Sealed tube;	72%

: 762-51-6
1-fluoro-2-iodoethane

: 79794-75-5
loratadine

: C24H27FN2O2

Conditions

Conditions	Yield
With manganese; 4,4'-Dimethoxy-2,2'-bipyridin; magnesium chloride; nickel dibromide In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	70%
With manganese; 4,4'-Dimethoxy-2,2'-bipyridin; magnesium chloride; nickel dibromide In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Inert atmosphere; Sealed tube;	70%

: 79794-75-5
loratadine

A: 79779-58-1
ethyl 4-(5,6-dihydro-11H-benzo[5,6]cyclohepta-[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

B: methyl 4-(5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
With tert-Amyl alcohol; tetramethyl ammoniumhydroxide; 2-(2-ethylhexyl)-6,8,11-tris(4-methoxyphenyl)-1H-peryleno[1,12-efg]isoindole-1,3(2H)-dione In methanol at 20℃; for 48h; Birch Reduction; Sealed tube; Irradiation;	A 65% B 26%

: 127-19-5
N,N-dimethyl acetamide

: 79794-75-5
loratadine

: C26H31N3O3

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; [2,2]bipyridinyl; nickel(II) bromide dimethoxyethane at 30℃; for 48h; Inert atmosphere; Irradiation; regioselective reaction;	63%

: 1279123-63-5
potassium hydrogenfluoride

: 79794-75-5
loratadine

: 73183-34-3
bis(pinacol)diborane

: ethyl 4-(8-(trifluoro-λ4-boraneyl)-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate potassium salt

Conditions

Conditions	Yield
Stage #1: loratadine; bis(pinacol)diborane With 10H-phenothiazine; caesium carbonate In acetonitrile at 45℃; for 72h; Irradiation; Sealed tube; Inert atmosphere; Stage #2: With hydrogenchloride; dihydroxy-methyl-borane In water; acetone Stage #3: potassium hydrogenfluoride Further stages;	62%

...Expand

: 79794-75-5
loratadine

tert-butyl halide: tert-butyl halide

: C26H31ClN2O2

Conditions

Conditions	Yield
With tris-(trimethylsilyl)silane; [Ir[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine]2(4,4′-di-t-Bu-2,2′-bipyridine)]PF6; oxygen; trifluoroacetic acid In acetone at 20℃; for 24h; Minisci Aromatic Substitution; Irradiation; regioselective reaction;	61%

: 79794-75-5
loratadine

: 4381-25-3
S-methyl-S-phenylsulfoximine

: ethyl 4-(8-((methyl(oxo)(phenyl)-λ6-sulfaneylidene)amino)-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
With nickel(II) bromide dimethoxyethane; 4,4'-Dimethoxy-2,2'-bipyridin; tetrabutylammomium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 20℃; for 8h; Inert atmosphere; Sealed tube; Electrochemical reaction;	60%

: 1768-64-5
4-chlorotetrahydro-2H-pyran

: 79794-75-5
loratadine

: ethyl 4-(8-(tetrahydro-2H-pyran-4-yl)-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
With 2,2'-biimidazole; (1,2-dimethoxyethane)dichloronickel(II); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; N-(adamantan-1-yl)-1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilan-2-amine In tert-Amyl alcohol; N,N-dimethyl acetamide at 55℃; for 18h; Inert atmosphere; Irradiation;	58%

: 79794-75-5
loratadine

: 149-73-5
trimethyl orthoformate

: 130642-61-4
ethyl 4-(8-methyl-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: loratadine; trimethyl orthoformate With potassium phosphate; [nickel(II)dichloride(dimethoxyethane)]; [4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine-N1,N1]bis-{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine at 20℃; for 72h; Irradiation; Sealed tube; Stage #2: With palladium on activated charcoal; hydrogen In methanol at 20℃; under 1551.49 Torr; for 10h;	57%
With potassium phosphate; [nickel(II)dichloride(dimethoxyethane)]; [4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine-N1,N1]bis-{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine at 20℃; for 72h; Irradiation; Sealed tube;	51%

Yield

Stage #1: loratadine; trimethyl orthoformate With potassium phosphate; [nickel(II)dichloride(dimethoxyethane)]; [4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine-N1,N1]bis-{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine at 20℃; for 72h; Irradiation; Sealed tube;
Stage #2: With palladium on activated charcoal; hydrogen In methanol at 20℃; under 1551.49 Torr; for 10h;

57%

With potassium phosphate; [nickel(II)dichloride(dimethoxyethane)]; [4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine-N1,N1]bis-{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine at 20℃; for 72h; Irradiation; Sealed tube;

51%

: 79794-75-5
loratadine

: 77970-95-7
S-(4-methoxyphenyl)-S-methylsulfoximine

: ethyl 4-(8-(((4-methoxyphenyl)(methyl)(oxo)-λ6-sulfaneylidene)amino)-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
With nickel(II) bromide dimethoxyethane; 4,4'-Dimethoxy-2,2'-bipyridin; tetrabutylammomium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 20℃; for 8h; Inert atmosphere; Sealed tube; Electrochemical reaction;	57%

: 10273-89-9
2-(2-methylphenyl)pyridine

: 79794-75-5
loratadine

: C34H33N3O2

Conditions

Conditions	Yield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 72h; Inert atmosphere;	56%
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 72h; Inert atmosphere; Glovebox;	56%

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 13675-18-8
tetrahydroxydiboron

: 79794-75-5
loratadine

: ethyl 4-(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-11Hbenzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: tetrahydroxydiboron; loratadine With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos In ethanol at 80℃; Stage #2: 2,3-dimethyl-2,3-butane diol In dichloromethane at 20℃; for 16h;	52%

...Expand

Loratadine Chemical Properties

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

Loratadine History

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

Loratadine Uses

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

Loratadine Safety Profile

Hazard Codes: Irritant Xi
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.

Loratadine 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).

Product Name

Loratadine

Synthetic route

Loratadine Chemical Properties

Loratadine History

Loratadine Uses

Loratadine Safety Profile

Loratadine Specification

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