(Z)-11-(3-dimethylaminopropylidene)-6,11-dihydro-dibenz-[b,e]oxepine-2-acetic acid hydrobromide
olopatadine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 5 - 25℃; for 20 - 21.0833h; pH=6.8 - 7.2; Product distribution / selectivity; | 96.09% |
In water at 20 - 25℃; for 16h; pH=6.8 - 7.2; Product distribution / selectivity; Alkaline conditions; | 92.3% |
Stage #1: (Z)-11-(3-dimethylaminopropylidene)-6,11-dihydro-dibenz-[b,e]oxepine-2-acetic acid hydrobromide With sodium hydroxide In water; toluene at 20 - 25℃; pH=> 12; Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=6.8 - 7.2; | 90% |
(Z)-11-<3-(dimethylamino)propylidene>-6,11-dihydrodibenzoxepin-2-acetic acid methyl ester
olopatadine
Conditions | Yield |
---|---|
Stage #1: (Z)-11-<3-(dimethylamino)propylidene>-6,11-dihydrodibenzoxepin-2-acetic acid methyl ester With methanol; sodium hydroxide; water at 20℃; for 5h; Stage #2: With hydrogenchloride In methanol; water Stage #3: In methanol; water | 92% |
With water; sodium hydroxide In methanol at 20℃; for 3h; | 88% |
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-bromopropylamine With zinc dibromide In tetrahydrofuran at 10 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: With naphthalene; lithium In tetrahydrofuran at 65 - 70℃; Inert atmosphere; Stage #3: isoxepac In tetrahydrofuran at 0 - 25℃; for 16.5h; Reagent/catalyst; Temperature; | 81.2% |
isoxepac
anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide
olopatadine
Conditions | Yield |
---|---|
Stage #1: anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 20 - 45℃; Inert atmosphere; Large scale; Stage #2: isoxepac In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 20℃; Solvent; Wittig Olefination; Large scale; | 55.63% |
olopatadine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate | 49% |
11-[(Z)-3-(dimethylamino)-propylidene]-6,11-dihydrodibenzo[b,e]oxepin-2-acetamide p-toluensulfonate
olopatadine
Conditions | Yield |
---|---|
Stage #1: 11-[(Z)-3-(dimethylamino)-propylidene]-6,11-dihydrodibenzo[b,e]oxepin-2-acetamide p-toluensulfonate With sodium hydrogencarbonate In methanol; dichloromethane; water for 0.25h; Stage #2: With water; potassium hydroxide In methanol; dichloromethane at 70℃; for 8h; Stage #3: With hydrogenchloride In methanol; dichloromethane; water at 20℃; pH=11; | 44.3% |
olopatadine
(Z)-11-[3-(dimethylamino)propylidene]-6,11-dihydro-dibenz[b,e]oxepin-2-acetic acid butyl ester
olopatadine
Conditions | Yield |
---|---|
Stage #1: (Z)-11-[3-(dimethylamino)propylidene]-6,11-dihydro-dibenz[b,e]oxepin-2-acetic acid butyl ester With potassium hydroxide In water at 5 - 70℃; for 4h; Stage #2: With sodium hydroxide In water; toluene at 20 - 25℃; Stage #3: With hydrogenchloride In water; acetone; toluene at 20 - 25℃; pH=2.5 - 3.0; |
3-(N,N-dimethylamino)propylmagnesium chloride
A
olopatadine
B
11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene; tetrahydrofuran / 2.08 h / 5 - 18 °C 2: hydrogenchloride / toluene / 7 h / 90 °C View Scheme |
A
olopatadine
B
11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid
Conditions | Yield |
---|---|
With hydrogenchloride In toluene at 90℃; for 7h; | A n/a B n/a |
isoxepac
A
olopatadine
B
11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid
Conditions | Yield |
---|---|
Stage #1: isoxepac; 3-dimethylaminopropyltriphenylphosphine hydrobromide With sodium hydride In tetrahydrofuran at 20 - 60℃; for 4h; Inert atmosphere; Large scale; Stage #2: at 20℃; Inert atmosphere; Large scale; Overall yield = 62.5 %; Overall yield = 2.36 kg; |
4-(2-methoxycarbonylbenzyloxy)phenyl acetic acid
A
olopatadine
B
11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / ethanol / 3 h / Reflux; Large scale 1.2: pH 1 - 2 / Large scale 2.1: acetic anhydride / 2 h / 80 - 90 °C / Large scale 3.1: sodium hydride / tetrahydrofuran / 4 h / 20 - 60 °C / Inert atmosphere; Large scale 3.2: 20 °C / Inert atmosphere; Large scale View Scheme |
4-(2-carboxybenzyloxy) phenyl acetic acid
A
olopatadine
B
11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: acetic anhydride / 2 h / 80 - 90 °C / Large scale 2.1: sodium hydride / tetrahydrofuran / 4 h / 20 - 60 °C / Inert atmosphere; Large scale 2.2: 20 °C / Inert atmosphere; Large scale View Scheme |
o-(chloromethyl)benzoic acid methyl ester
A
olopatadine
B
11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / ethanol / 24 h / Reflux 2.1: potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / ethanol / 3 h / Reflux; Large scale 2.2: pH 1 - 2 / Large scale 3.1: acetic anhydride / 2 h / 80 - 90 °C / Large scale 4.1: sodium hydride / tetrahydrofuran / 4 h / 20 - 60 °C / Inert atmosphere; Large scale 4.2: 20 °C / Inert atmosphere; Large scale View Scheme |
Methyl 4-hydroxyphenylacetate
A
olopatadine
B
11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / ethanol / 24 h / Reflux 2.1: potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / ethanol / 3 h / Reflux; Large scale 2.2: pH 1 - 2 / Large scale 3.1: acetic anhydride / 2 h / 80 - 90 °C / Large scale 4.1: sodium hydride / tetrahydrofuran / 4 h / 20 - 60 °C / Inert atmosphere; Large scale 4.2: 20 °C / Inert atmosphere; Large scale View Scheme |
Methyl 4-hydroxyphenylacetate
olopatadine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C 2: iodine; silver sulfate / methanol / 2.25 h / 20 °C 3: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere 4: piperidine; formic acid; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 4 h / 95 °C / Inert atmosphere 5: pyridine / 0 - 90 °C 6: methanol; water / 3 h / Reflux 7: sodium hydroxide; water / methanol / 3 h / 20 °C View Scheme |
1-Bromo-2-bromomethyl-benzene
olopatadine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C 2: iodine; silver sulfate / methanol / 2.25 h / 20 °C 3: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere 4: piperidine; formic acid; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 4 h / 95 °C / Inert atmosphere 5: pyridine / 0 - 90 °C 6: methanol; water / 3 h / Reflux 7: sodium hydroxide; water / methanol / 3 h / 20 °C View Scheme |
methyl 2-{4-[(2-bromobenzyl)oxy]phenyl}acetate
olopatadine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: iodine; silver sulfate / methanol / 2.25 h / 20 °C 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere 3: piperidine; formic acid; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 4 h / 95 °C / Inert atmosphere 4: pyridine / 0 - 90 °C 5: methanol; water / 3 h / Reflux 6: sodium hydroxide; water / methanol / 3 h / 20 °C View Scheme |
methyl 2-{4-[(2-bromobenzyl)oxy]-3-iodophenyl}acetate
olopatadine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere 2: piperidine; formic acid; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 4 h / 95 °C / Inert atmosphere 3: pyridine / 0 - 90 °C 4: methanol; water / 3 h / Reflux 5: sodium hydroxide; water / methanol / 3 h / 20 °C View Scheme |
methyl 2-{4-[(2-bromobenzyl)oxy]-3-(4-hydroxybut-1-yn-1-yl)phenyl}acetate
olopatadine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: piperidine; formic acid; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 4 h / 95 °C / Inert atmosphere 2: pyridine / 0 - 90 °C 3: methanol; water / 3 h / Reflux 4: sodium hydroxide; water / methanol / 3 h / 20 °C View Scheme |
(Z)-methyl 2-[11-(3-hydroxypropylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl]acetate
olopatadine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine / 0 - 90 °C 2: methanol; water / 3 h / Reflux 3: sodium hydroxide; water / methanol / 3 h / 20 °C View Scheme |
olopatadine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol; water / 3 h / Reflux 2: sodium hydroxide; water / methanol / 3 h / 20 °C View Scheme |
isoxepac
olopatadine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 1-methyl-1H-imidazole; di-tert-butyl dicarbonate; triethylamine / toluene / 8.5 h / 50 °C 2.1: tetrahydrofuran / 2.5 h / 15 - 20 °C 2.2: 0.5 h 3.1: hydrogenchloride / toluene; water / 6 h / 100 °C View Scheme |
tert-butyl 11-hydroxy-11-(3’-dimethylaminopropyl)-6,11-dihydrodibenzo[b,e]oxepin-2-acetate
olopatadine
Conditions | Yield |
---|---|
With hydrogenchloride In water; toluene at 100℃; for 6h; |
olopatadine
olopatadine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetone at 5 - 25℃; for 2 - 15h; Product distribution / selectivity; | 95.6% |
With hydrogenchloride In water; acetone at 0 - 25℃; for 16 - 22h; Product distribution / selectivity; | 88.1% |
With hydrogenchloride In water; acetone at 20 - 60℃; Product distribution / selectivity; | 81.2% |
With hydrogenchloride In water | |
With hydrogenchloride In tetrahydrofuran; water at 15 - 20℃; for 0.75 - 0.833333h; pH=0 - 1; Heating / reflux; |
N,O-dimethylhydroxylamine*hydrochloride
olopatadine
(Z)-2-(11-(3-(dimethylamino)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl)-N-methoxy-N-methylacetamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 16h; | 37% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 16h; | 37% |
olopatadine
(Z)-11-<3-(dimethylamino)propylidene>-2-(2-hydroxyethyl)-6,11-dihydrodibenzoxepin
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Ambient temperature; | 11% |
olopatadine
Conditions | Yield |
---|---|
With hydrogen bromide at 100℃; for 2h; |
olopatadine
C21H23NO2
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C 2: diisobutylaluminium hydride / dichloromethane; hexanes / 1 h / -78 °C View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C 2: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 °C View Scheme |
olopatadine
(Z)-2-(11-(3-(dimethylamino)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetaldehyde oxime
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C 2: diisobutylaluminium hydride / dichloromethane; hexanes / 1 h / -78 °C 3: hydroxylamine hydrochloride; triethylamine / dichloromethane; hexanes; methanol / 5 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C 2: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 °C 3: triethylamine; hydroxylamine hydrochloride / dichloromethane; methanol; hexane / 5 h / 20 °C View Scheme |
olopatadine
(Z)-2-(11-(3-(dimethylamino)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetaldehyde O-methyl oxime
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C 2: diisobutylaluminium hydride / dichloromethane; hexanes / 1 h / -78 °C 3: triethylamine / dichloromethane; hexanes; methanol / 5 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C 2: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 °C 3: triethylamine / dichloromethane; methanol; hexane / 5 h / 20 °C View Scheme |
The CAS register number of Dibenz[b,e]oxepin-2-aceticacid, 11-[3-(dimethylamino)propylidene]-6,11-dihydro-, (11Z)- is 113806-05-6. It also can be called as 11-((Z)-3-(Dimethyl-amino)propylidene)-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid and the IUPAC name about this chemical is 2-[(11E)-11-[3-(dimethylamino)propylidene]-6H-benzo[c][1]benzoxepin-2-yl]acetic acid. The molecular formula about this chemical is C21H23NO3 and the molecular weight is 337.42. Classification code about this chemical are Analgesics, Analgesics, Non-Narcotic, Anti-Inflammatory Agents, Anti-allergic agents, Anti-inflammatory agents, non-steroidal, Antirheumatic Agents, Histamine Agents, Histamine Antagonists, Histamine H1 Antagonists, Non-Sedating, Histamine H1 antagonists, Neurotransmitter Agents, Peripheral Nervous System Agents and Sensory System Agents.
Physical properties about Dibenz[b,e]oxepin-2-aceticacid, 11-[3-(dimethylamino)propylidene]-6,11-dihydro-, (11Z)- are: (1)ACD/LogP: 3.14; (2)ACD/LogD (pH 5.5): 0.63; (3)ACD/LogD (pH 7.4): 0.64; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 3.71; (7)ACD/KOC (pH 7.4): 3.82; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 38.77Å2; (12)Index of Refraction: 1.64; (13)Molar Refractivity: 99.62 cm3; (14)Molar Volume: 276.2 cm3; (15)Polarizability: 39.49x10-24cm3; (16)Surface Tension: 56 dyne/cm; (17)Enthalpy of Vaporization: 83.86 kJ/mol; (18)Boiling Point: 523 °C at 760 mmHg; (19)Vapour Pressure: 9.11E-12 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)Cc2ccc1OCc3c(C(\c1c2)=C/CCN(C)C)cccc3
(2)InChI: InChI=1/C21H23NO3/c1-22(2)11-5-8-18-17-7-4-3-6-16(17)14-25-20-10-9-15(12-19(18)20)13-21(23)24/h3-4,6-10,12H,5,11,13-14H2,1-2H3,(H,23,24)/b18-8+
(3)InChIKey: JBIMVDZLSHOPLA-QGMBQPNBBL
(4)Std. InChI: InChI=1S/C21H23NO3/c1-22(2)11-5-8-18-17-7-4-3-6-16(17)14-25-20-10-9-15(12-19(18)20)13-21(23)24/h3-4,6-10,12H,5,11,13-14H2,1-2H3,(H,23,24)/b18-8+
(5)Std. InChIKey: JBIMVDZLSHOPLA-QGMBQPNBSA-N
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