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oxalic acid
(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile
escitalopram oxalate
Conditions | Yield |
---|---|
Stage #1: (S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile With methanesulfonyl chloride; triethylamine In dichloromethane at 5℃; for 2h; Stage #2: oxalic acid | 65% |
Stage #1: (S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile With potassium carbonate; 2,5-dichloronitrobenzene In dimethyl sulfoxide at 20 - 100℃; for 15h; Stage #2: oxalic acid In acetone at 30℃; | |
Stage #1: (S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile With bis(phenyl) carbonate; sodium methylate In acetonitrile at 79 - 80℃; for 4h; Stage #2: oxalic acid In ethyl acetate for 3h; Reagent/catalyst; Reflux; | 3.02 g |
Conditions | Yield |
---|---|
Stage #1: (1S)-4-[4-(dimethylamino)-1-(4'-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hemi-(+)-di-(p-toluoyl) tartaric acid salt With sodium hydroxide In diethyl ether; water at 25℃; for 0.5h; Stage #2: With triethylamine In diethyl ether; water; toluene at 5℃; for 0.5h; Stage #3: oxalic acid Further stages; | 85% |
Stage #1: (1S)-4-[4-(dimethylamino)-1-(4'-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hemi-(+)-di-(p-toluoyl) tartaric acid salt With ammonia In dichloromethane; water pH=9; Stage #2: With triethylamine; p-toluenesulfonyl chloride In dichloromethane at 5℃; for 1h; Stage #3: oxalic acid In acetone | n/a |
Conditions | Yield |
---|---|
Stage #1: (S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(4-nitrobenzoyloxymethyl)benzonitrile hydrochloride With sodium hydrogencarbonate In water; ethyl acetate Stage #2: With potassium carbonate In dimethyl sulfoxide at 90 - 100℃; for 2h; Stage #3: oxalic acid | 82% |
Conditions | Yield |
---|---|
In acetone at 25 - 30℃; Industry scale; | 98.57% |
In acetonitrile at 50℃; for 0.5h; | 89% |
In acetone at 25 - 45℃; for 1.5h; | 85% |
(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(2-nitro-4-chlorophenoxymethyl)benzonitrile hydrochloride
oxalic acid
escitalopram oxalate
Conditions | Yield |
---|---|
Stage #1: (S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(2-nitro-4-chlorophenoxymethyl)benzonitrile hydrochloride With potassium carbonate at 100℃; for 0.5h; Stage #2: oxalic acid | 64% |
Conditions | Yield |
---|---|
Stage #1: 1-(3-aminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; (-)-di-p-toluoyl tartaric acid salt With sodium hydroxide In water; toluene pH=11 - 13; Stage #2: formaldehyd; formic acid In water at 95 - 100℃; for 3 - 4h; Stage #3: oxalic acid With hydrogenchloride more than 3 stages; |
Conditions | Yield |
---|---|
Stage #1: (S)-citalopram (L)-tartrate With sodium hydroxide In water; ethyl acetate pH=10; Stage #2: oxalic acid In ethyl acetate |
escitalopram
escitalopram oxalate
Conditions | Yield |
---|---|
With oxalic acid In acetone at 10℃; for 1h; | |
With oxalic acid In ethanol at 5 - 20℃; for 10.5h; Product distribution / selectivity; |
oxalic acid
escitalopram oxalate
Conditions | Yield |
---|---|
Stage #1: escitalopram With hydrogen bromide In isopropyl alcohol at 20℃; for 2.16667h; pH=3.5 - 4; Stage #2: With ammonia In water; ethyl acetate for 0.5h; pH=9 - 9.5; Stage #3: oxalic acid In isopropyl alcohol at 20 - 40℃; for 2.16667h; Purification / work up; | |
Stage #1: oxalic acid With ammonia In water; ethyl acetate pH=9 - 9.5; Stage #2: oxalic acid In isopropyl alcohol at 20 - 40℃; for 2.16667h; Purification / work up; | |
Stage #1: (+)-(S)-citalopram hydrobromide With ammonia In water; ethyl acetate pH=9 - 9.5; Stage #2: oxalic acid In isopropyl alcohol at 20 - 40℃; for 2.16667h; Purification / work up; |
4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile
escitalopram oxalate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: isopropyl alcohol / 3 h / 20 - 45 °C 2.1: ammonia / water / pH ~ 9 2.2: 3 h / -5 °C 3.1: isopropyl alcohol / 0.5 h / 50 - 60 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: isopropyl alcohol / 25 - 70 °C / Resolution of racemate 2.1: ammonium hydroxide / dichloromethane; water / 1 h / 5 - 15 °C 2.2: -5 - 5 °C 3.1: acetone / 20 - 40 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: isopropyl alcohol / 25 - 35 °C 2.1: sodium hydroxide / diethyl ether; water / 0.5 h / 25 °C 3.1: triethylamine / toluene / 0.5 h / 5 °C 3.2: 1 h / 5 °C 4.1: acetone / 1.5 h / 25 - 45 °C View Scheme |
Molecule structure of Escitalopram oxalate (CAS NO.219861-08-2):
IUPAC Name: (1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile; oxalic acid
Molecular Weight: 414.426823 g/mol
Molecular Formula: C22H23FN2O5
Melting Point: 152-153 °C
Boiling Point: 428.3 °C at 760 mmHg
Flash Point: 212.8 °C
Enthalpy of Vaporization: 68.35 kJ/mol
Vapour Pressure: 1.53E-07 mmHg at 25 °C
H-Bond Donor: 2
H-Bond Acceptor: 8
Rotatable Bond Count: 6
Exact Mass: 414.1591
MonoIsotopic Mass: 414.1591
Topological Polar Surface Area: 111
Heavy Atom Count: 30
Complexity: 537
Defined Atom StereoCenter Count: 1
Canonical SMILES: CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F.C(=O)(C(=O)O)O
Isomeric SMILES: CN(C)CCC[C@@]1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F.C(=O)(C(=O)O)O
InChI: InChI=1S/C20H21FN2O.C2H2O4/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20;3-1(4)2(5)6/h4-9,12H,3,10-11,14H2,1-2H3;(H,3,4)(H,5,6)/t20-;/m0./s1
InChIKey: KTGRHKOEFSJQNS-BDQAORGHSA-N
Product Categories: Antidepressant; Heterocyclic Compounds; Intermediates & Fine Chemicals; Neurochemicals; Pharmaceuticals; Isotope Labeled Compounds; Escitalopram
Escitalopram oxalate (219861-08-2) was developed in the cooperation between Forest Laboratories and Lundbeck. Its development began in the summer of 1997, and the resulting new drug application was submitted to the U.S. Food and Drug Administration (FDA) in March 2001.Because of the previous extensive experience of Lundbeck and Forest with citalopram,it only took 3.5 years to develop escitalopram.The FDA issued the approval of escitalopram for generalized anxiety disorder in December 2003 and major depression in August 2002. Escitalopram can be considered an example of the strategy pharmaceutical companies use in order to extend a drug's lifetime, in this case of the citalopram franchise. Escitalopram is an enantiopure compound of the racemic mixture citalopram, used for the same indication, and for that reason it required less investment and less time to develop. Two years after escitalopram's launch, when the patent on citalopram expired, the escitalopram sales successfully made up for the loss. On May 23, 2006, the FDA approved a generic version of escitalopram by Teva.On July 14 of that year, however, the U.S. District Court of Delaware decided in favor of Lundbeck regarding the patent infringement dispute and ruled the patent on escitalopram valid.In 2006 Forest Laboratories was granted an 828 day extension on its patent for escitalopram. The patent expiry was pushed from December 7, 2009 to March 14, 2012.
Escitalopram oxalate (CAS NO.219861-08-2) is used as an inhibitor of serotonin (5-HT) uptake.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
Escitalopram oxalate (CAS NO.219861-08-2) is also named as Cipralex ; Lexapro ; Lu 26-054-0 ; S-(+)-1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile oxalate ; S-(+)-5-Isobenzofurancarbonitrile, 1-(3-
(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, oxalate ; UNII-5U85DBW7LO ; 5-Isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, (1S)-, ethanedioate (1:1) . Escitalopram oxalate (CAS NO.219861-08-2) is white solid. It is soluble in methanol and dimethyl sulfoxide, dissolved in saline, slightly soluble in water and ethanol, slightly soluble in ethyl acetate, insoluble in heptane.