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inquiryProduct Name: Citalopram Other Name Celexa, Cipramil CAS: 59729-33-8 MF: C20H21FN2
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Citalopram cas 59729-33-8 Purity: 99% Min Application: Intermediates Appearance: Powder Package: Bag Delivery: 3-5days Our Advantage & Service 1.Top quality: Using high quality material and establishing a strict quality control syste
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inquiryCompany Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments
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inquirycitalopram hydrobromide
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With sodium hydroxide In water | 100% |
With sodium hydroxide In water; toluene for 0.25h; pH=10; | 93% |
With ammonia In water at 20℃; for 3h; pH=9; Product distribution / selectivity; | |
With sodium hydroxide In water; toluene at 20℃; pH=9 - 10; Industry scale; |
3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile
3-(N,N-dimethylamino)propylmagnesium chloride
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With ammonium chloride In tetrahydrofuran; water; toluene | 95% |
With hydrogen bromide In tetrahydrofuran; 1,2-dimethoxyethane | 75% |
1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
3-(Dimethylamino)propyl chloride
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; 3-(Dimethylamino)propyl chloride With sodium hydride In 1,3-dimethyl-2-imidazolidinone; toluene at 40 - 50℃; for 0.666667h; Stage #2: With hydrogenchloride; water at 65 - 70℃; for 3h; Stage #3: With sodium hydroxide In water; toluene Product distribution / selectivity; | 93% |
Stage #1: 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; 3-(Dimethylamino)propyl chloride With sodium hydride In tetrahydrofuran; toluene at 40 - 50℃; for 0.666667h; Stage #2: With dimethyl sulfoxide at 65 - 70℃; for 3h; Stage #3: With acetic acid In water; toluene Product distribution / selectivity; | 51.6% |
With sodium hydride In dimethyl sulfoxide; toluene at 20 - 25℃; for 3h; Product distribution / selectivity; |
1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With trichlorophosphate In acetonitrile at 60℃; Heating / reflux; | 92% |
Stage #1: 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide With thionyl chloride In toluene at 85 - 95℃; for 1h; Stage #2: With ammonia In water; toluene pH=7.5 - 7.8; Purification / work up; |
copper(I) cyanide
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
Stage #1: dl-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-5-bromo-1,3-dihydroisobenzofuran oxalate salt; copper(I) cyanide With copper(l) iodide In DMF (N,N-dimethyl-formamide) at 145 - 150℃; for 28h; Stage #2: With ethylenediamine In DMF (N,N-dimethyl-formamide); water at 25 - 30℃; for 2h; | 87% |
4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile With phosphoric acid In toluene at 80℃; for 2.5h; Stage #2: With sodium hydroxide In water; toluene at 50℃; pH=10; | 86% |
With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃; for 3h; | 55% |
With triphenylphosphine; sodium t-butanolate; diethylazodicarboxylate In tetrahydrofuran at 0℃; | |
With sulfuric acid In water at 70℃; for 6h; Product distribution / selectivity; |
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
Stage #1: potassium cyanide With acetic acid In ethylene glycol Sealed tube; Stage #2: 3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine With P(t-Bu)3 Palladacycle Gen. 3; potassium acetate In 1,4-dioxane; water at 60℃; for 16h; Sealed tube; | 86% |
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine With sodium cyanide; copper(I) cyanide In DMF (N,N-dimethyl-formamide); toluene at 154 - 159℃; Heating / reflux; Stage #2: With sodium cyanide In DMF (N,N-dimethyl-formamide); water at 60 - 70℃; Stage #3: With ethylenediamine In DMF (N,N-dimethyl-formamide); water; toluene | 84% |
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
pyrographite
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide; toluene | 84% |
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 150℃; for 24h; Rosenmund-van Braun Cyanation; Sealed tube; Inert atmosphere; | 74% |
1-cyanobenzotriazole
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With ammonium chloride In tetrahydrofuran; water; toluene | 71.4% |
3-(5-(aminomethyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
A
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With ammonium hydroxide; hydrogen bromide; copper(I) chloride; silica gel In pyridine; n-heptane; isopropyl alcohol; acetone | A 14% B 66% |
dimethyl amine
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
Stage #1: C19H16FNO With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide Stage #2: dimethyl amine With sodium tris(acetoxy)borohydride | 62% |
4,4-dimethyl-[2-[3-hydroxymethyl-4-[4-fluoro-a-hydroxy-a-(dimethylamino)propyl]benzyl]phenyl]oxazoline
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 4,4-dimethyl-[2-[3-hydroxymethyl-4-[4-fluoro-a-hydroxy-a-(dimethylamino)propyl]benzyl]phenyl]oxazoline With pyridine; thionyl chloride at 20 - 25℃; for 1h; Stage #2: With trichlorophosphate for 4h; | 48% |
With pyridine; trichlorophosphate at 20 - 90℃; for 5h; | 38% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With NaCN; sulfuric acid; sodium carbonate; sodium nitrite; CuCN In water; toluene | 32% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With sodium hydroxide In water Conversion of starting material; |
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
copper(I) cyanide
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine; copper(I) cyanide at 140 - 150℃; for 6h; Stage #2: With N,N-dimethyl-formamide at 140 - 150℃; for 0.0833333h; Stage #3: With ethylenediamine In water; toluene at 80℃; for 0.416667h; | |
With alpha-D-glucopyranose; potassium iodide In DMF (N,N-dimethyl-formamide) at 140 - 160℃; |
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
copper(I) cyanide
A
rac-desmethylcitalopram
B
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
at 140 - 150℃; | |
In DMF (N,N-dimethyl-formamide) at 40 - 165℃; for 6.5 - 8.5h; |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With ammonia In water; toluene | |
With ammonia In water pH=9.0 - 9.2; | |
With ammonia In water for 0.5h; pH=6.2 - 9.2; Product distribution / selectivity; |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With phosphoric acid In tetrahydrofuran; water at 10 - 80℃; |
formaldehyd
rac-desmethylcitalopram
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
Stage #1: formaldehyd; rac-desmethylcitalopram With formic acid In chloroform for 8h; Heating / reflux; Stage #2: With ammonia In chloroform; water at 20℃; pH=8 - 9; |
4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile
A
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
B
1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide
Conditions | Yield |
---|---|
Stage #1: 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile With phosphoric acid In water at 105℃; for 14h; Stage #2: With ammonia In water pH=8 - 10; Purification / work up; |
formaldehyd
formic acid
didesmethylcitalopram
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
In water at 95 - 100℃; for 12h; Heating / reflux; |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 3h; pH=9; Product distribution / selectivity; |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With ammonia In water; toluene at 10 - 15℃; Product distribution / selectivity; |
C2H4O2*C20H21FN2O
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 3h; pH=9; Product distribution / selectivity; |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Di-p-toluoyl-L-tartaric acid
C20H18O8*C20H21FN2O
Conditions | Yield |
---|---|
In isopropyl alcohol Reflux; | 100% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide
Conditions | Yield |
---|---|
Stage #1: 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile In dimethyl sulfoxide for 0.5h; Stage #2: With dihydrogen peroxide In dimethyl sulfoxide Cooling with ice; Inert atmosphere; | 95% |
With dihydrogen peroxide; potassium hydroxide In ethanol; dimethyl sulfoxide at 60℃; for 2h; | 49% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
3-(5-(aminomethyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere; Reflux; | 94% |
With hydrogen In para-xylene at 130℃; under 750.075 Torr; for 24h; chemoselective reaction; | 75% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
citalopram hydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide In water; toluene at 5 - 10℃; Heating / reflux; | 93.6% |
With hydrogen bromide In water; isopropyl alcohol pH=6 - 7; | 88.2% |
Stage #1: 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile With hydrogen bromide In acetone at 20 - 25℃; Gas phase; Stage #2: Stage #3: In water | 77.3% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
1,1-difluoro-2,2-diphenylethylene
Conditions | Yield |
---|---|
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; sodium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; Irradiation; | 84% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; sodium acetate In N,N-dimethyl-formamide at 20℃; for 16h; Irradiation; Inert atmosphere; diastereoselective reaction; | 82% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With C10H12O2NiC8H12-1,5-cyclo; triphenylborane; diphenyl(methyl)phosphine In 1-methyl-pyrrolidin-2-one at 80℃; for 18h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube; | 75% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
methylmagnesium bromide
Conditions | Yield |
---|---|
Stage #1: 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile; methylmagnesium bromide In toluene Heating; Stage #2: With hydrogenchloride In water for 2h; Heating; | 73% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
With potassium tert-butylate; lithium hexamethyldisilazane at 120℃; for 24h; | 67% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
benzaldehyde
Conditions | Yield |
---|---|
Stage #1: triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane; benzaldehyde With copper(I) thiophene-2-carboxylate; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; sodium t-butanolate In toluene at 20℃; for 0.166667h; Inert atmosphere; Sealed tube; Stage #2: 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile In toluene at 80℃; for 3h; Inert atmosphere; Stage #3: With acetic acid In water; toluene for 1h; Inert atmosphere; | 64% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
4-(E)-4-(dimethylamino)-1-(4-fluorophenyl)but-1-enyl-3-(hydroxymethyl)benzonitrile
C40H41F2N4O(1+)*Cl(1-)
Conditions | Yield |
---|---|
With methanesulfonyl chloride; triethylamine In dichloromethane for 24h; Reflux; | 45% |
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
(2S,3S)-di-4-toluoyltartaric acid
C20H18O8*C20H21FN2O
Conditions | Yield |
---|---|
Stage #1: 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile; (2S,3S)-di-4-toluoyltartaric acid In acetonitrile at 20℃; Stage #2: In methanol; acetonitrile at 0 - 75℃; | 36% |
Stage #1: 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile; (2S,3S)-di-4-toluoyltartaric acid In acetonitrile at 20℃; for 1h; Resolution of racemate; Stage #2: With sodium hydroxide In water Stage #3: (2S,3S)-di-4-toluoyltartaric acid optical yield given as %ee; Further stages; | 11% |
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