Product Name

  • Name

    Citalopram

  • EINECS 261-891-1
  • CAS No. 59729-33-8
  • Article Data57
  • CAS DataBase
  • Density 1.18 g/cm3
  • Solubility
  • Melting Point 182-183 °C
  • Formula C20H21FN2O
  • Boiling Point 428.3 °C at 760 mmHg
  • Molecular Weight 324.398
  • Flash Point 212.8 °C
  • Transport Information UN 3249
  • Appearance grease
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 59729-33-8 (Citalopram)
  • Hazard Symbols
  • Synonyms 1-(3-Dimethylaminopropyl)-1-(4-fluorophenyl)-5-cyanophthalan;1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile;Bonitrile;Lu 10-171;Nitalapram;
  • PSA 36.26000
  • LogP 3.81298

Synthetic route

citalopram hydrobromide
59729-32-7

citalopram hydrobromide

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In water100%
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
445312-08-3

3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile

3-(N,N-dimethylamino)propylmagnesium chloride
19070-16-7

3-(N,N-dimethylamino)propylmagnesium chloride

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With ammonium chloride In tetrahydrofuran; water; toluene95%
With hydrogen bromide In tetrahydrofuran; 1,2-dimethoxyethane75%
1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
64169-67-1

1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile

3-(Dimethylamino)propyl chloride
109-54-6

3-(Dimethylamino)propyl chloride

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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
64372-56-1

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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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;
dl-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-5-bromo-1,3-dihydroisobenzofuran oxalate salt

dl-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-5-bromo-1,3-dihydroisobenzofuran oxalate salt

copper(I) cyanide
544-92-3

copper(I) cyanide

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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
103146-25-4

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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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;
potassium cyanide

potassium cyanide

3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
64169-39-7

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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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
64169-39-7

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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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%
aqueous ethylenediamine

aqueous ethylenediamine

3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
64169-39-7

3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine

copper(l) cyanide

copper(l) cyanide

pyrographite
7440-44-0

pyrographite

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide; toluene84%
...Expand
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
64169-39-7

3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine

copper(l) cyanide

copper(l) cyanide

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 150℃; for 24h; Rosenmund-van Braun Cyanation; Sealed tube; Inert atmosphere;74%
3-[i-(4-fluorophenyl)-1,3 dihydro-isobenzofiran-1-yl]propylldirnethylamine 5-magnesium bromide

3-[i-(4-fluorophenyl)-1,3 dihydro-isobenzofiran-1-yl]propylldirnethylamine 5-magnesium bromide

[3-[1-(4-fluorophenyl)-1,3 dihydro-isobenzofuran-1-yl]propyl]dimethyl amine

[3-[1-(4-fluorophenyl)-1,3 dihydro-isobenzofuran-1-yl]propyl]dimethyl amine

1-cyanobenzotriazole
15328-32-2

1-cyanobenzotriazole

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With ammonium chloride In tetrahydrofuran; water; toluene71.4%
...Expand
3-(5-(aminomethyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
125803-03-4

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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

B

HBr salt of citalopram

HBr salt of citalopram

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen bromide; copper(I) chloride; silica gel In pyridine; n-heptane; isopropyl alcohol; acetoneA 14%
B 66%
C19H16FNO

C19H16FNO

dimethyl amine
124-40-3

dimethyl amine

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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
265137-38-0

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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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%
5-Amino-1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran

5-Amino-1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With NaCN; sulfuric acid; sodium carbonate; sodium nitrite; CuCN In water; toluene32%
Reaxys ID: 11465244

Reaxys ID: 11465244

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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
64169-39-7

3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine

copper(I) cyanide
544-92-3

copper(I) cyanide

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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
64169-39-7

3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine

copper(I) cyanide
544-92-3

copper(I) cyanide

A

rac-desmethylcitalopram
62498-67-3

rac-desmethylcitalopram

B

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
at 140 - 150℃;
In DMF (N,N-dimethyl-formamide) at 40 - 165℃; for 6.5 - 8.5h;
...Expand
Citalopram oxalate

Citalopram oxalate

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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;
Br(1-)*C20H22FN2O2(1-)*Mg(2+)

Br(1-)*C20H22FN2O2(1-)*Mg(2+)

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With phosphoric acid In tetrahydrofuran; water at 10 - 80℃;
formaldehyd
50-00-0

formaldehyd

rac-desmethylcitalopram
62498-67-3

rac-desmethylcitalopram

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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
103146-25-4

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
59729-33-8

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
64372-56-1

1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide

Conditions
ConditionsYield
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
50-00-0

formaldehyd

formic acid
64-18-6

formic acid

didesmethylcitalopram
62498-69-5

didesmethylcitalopram

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
In water at 95 - 100℃; for 12h; Heating / reflux;
...Expand
Citalopram hydrochloride

Citalopram hydrochloride

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 3h; pH=9; Product distribution / selectivity;
C20H21FN2O*H2O4S

C20H21FN2O*H2O4S

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With ammonia In water; toluene at 10 - 15℃; Product distribution / selectivity;
C2H4O2*C20H21FN2O
500733-84-6

C2H4O2*C20H21FN2O

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Di-p-toluoyl-L-tartaric acid
32634-66-5

Di-p-toluoyl-L-tartaric acid

C20H18O8*C20H21FN2O
1373405-39-0

C20H18O8*C20H21FN2O

Conditions
ConditionsYield
In isopropyl alcohol Reflux;100%
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

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
64372-56-1

1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide

Conditions
ConditionsYield
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
59729-33-8

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
125803-03-4

3-(5-(aminomethyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine

Conditions
ConditionsYield
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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

citalopram hydrobromide
59729-32-7

citalopram hydrobromide

Conditions
ConditionsYield
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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

1,1-difluoro-2,2-diphenylethylene
569-72-2

1,1-difluoro-2,2-diphenylethylene

C34H30F2N2O

C34H30F2N2O

Conditions
ConditionsYield
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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

C24H30N2O5S

C24H30N2O5S

C44H51FN4O6S

C44H51FN4O6S

Conditions
ConditionsYield
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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

2(13)CN(1-)*Zn(2+)

2(13)CN(1-)*Zn(2+)

C19(13)CH21FN2O

C19(13)CH21FN2O

Conditions
ConditionsYield
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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

methylmagnesium bromide
75-16-1

methylmagnesium bromide

1-[1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-yl]-ethanone

1-[1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-yl]-ethanone

Conditions
ConditionsYield
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
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

2-methyl-3-(phenylethynyl)benzo[b]thiophene

2-methyl-3-(phenylethynyl)benzo[b]thiophene

C37H33FN2OS

C37H33FN2OS

Conditions
ConditionsYield
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
59729-33-8

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
745783-97-5

triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

benzaldehyde
100-52-7

benzaldehyde

1-{10-[3-(dimethylamino)-2-methylpropyl]-10H-phenothiazin-3-yl}-2-phenyl-2-[(triethylsilyl)oxy]ethan-1-one

1-{10-[3-(dimethylamino)-2-methylpropyl]-10H-phenothiazin-3-yl}-2-phenyl-2-[(triethylsilyl)oxy]ethan-1-one

Conditions
ConditionsYield
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%
...Expand
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

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
1370643-23-4

4-(E)-4-(dimethylamino)-1-(4-fluorophenyl)but-1-enyl-3-(hydroxymethyl)benzonitrile

C40H41F2N4O(1+)*Cl(1-)
1370643-27-8

C40H41F2N4O(1+)*Cl(1-)

Conditions
ConditionsYield
With methanesulfonyl chloride; triethylamine In dichloromethane for 24h; Reflux;45%
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

(2S,3S)-di-4-toluoyltartaric acid
32634-68-7

(2S,3S)-di-4-toluoyltartaric acid

C20H18O8*C20H21FN2O
1373405-37-8

C20H18O8*C20H21FN2O

Conditions
ConditionsYield
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%

Citalopram History

   Citalopram (CAS NO.59729-33-8) (pronounced /sa??tæl?præm/) was originally created in 1989by the pharmaceutical company Lundbeck. The patent expired in 2003, allowing other companies to legally produce generic versions. Lundbeck has recently released an updated formulation called escitalopram (also known as Cipralex or Lexapro), which is the S-enantiomer of the racemic citalopram (see b), and acquired a new patent for it. In the United States, Forest Labs manufactures and markets the drug.

Citalopram Specification

The IUPAC name of Citalopram is 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile. With the CAS registry number 59729-33-8, it is also named as 5-Isobenzofurancarbonitrile, 1,3-dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-. The classification codes are Antidepressive Agents; Antidepressive agents, second-generation; Central Nervous System Agents; Drug / Therapeutic Agent; Human Data; Neurotransmitter Agents; Neurotransmitter Uptake Inhibitors; Psychotropic Drugs; Serotonin Agents; Serotonin uptake inhibitors. It is grease which can be crystallized from isopropanol.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.54; (4)ACD/LogD (pH 7.4): 0.39; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 4.19; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.591; (13)Molar Refractivity: 92.13 cm3; (14)Molar Volume: 272.6 cm3; (15)Polarizability: 36.52×10-24 cm3; (16)Surface Tension: 49.8 dyne/cm; (17)Enthalpy of Vaporization: 68.35 kJ/mol; (18)Vapour Pressure: 1.53E-07 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Exact Mass: 324.163792; (21)MonoIsotopic Mass: 324.163792; (22)Topological Polar Surface Area: 36.3; (23)Heavy Atom Count: 24; (24)Complexity: 466.

Preparation of Citalopram: It can be obtained by 1-(4-fluorophenyl) -1,3-dihydro-S-isobenzofuran nitrile.

Uses of Citalopram: It is highly selective and potent 5-HT uptake inhibitor with no effect on noradrenalin or dopamine uptake (IC 50 values are 1.8, 8800 and 41000 nM respectively). It also has negligible activity at a wide range of receptors and is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class to treat major depression. What's more, this drug is frequently used off-label to treat anxiety, panic disorder, ADHD, PMDD, Body dysmorphic disorder and OCD.

People can use the following data to convert to the molecule structure. 
1. SMILES:Fc1ccc(cc1)C3(OCc2cc(C#N)ccc23)CCCN(C)C
2. InChI:InChI=1/C20H21FN2O/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/h4-9,12H,3,10-11,14H2,1-2H3 
3. InChIKey:WSEQXVZVJXJVFP-UHFFFAOYAV

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 4571ug/kg/8D- (4.571mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: HEADACHE

GASTROINTESTINAL: NAUSEA OR VOMITING		 Human Psychopharmacology. Vol. 12, Pg. 119, 1997.
man LDLo oral 56mg/kg (56mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Lancet. Vol. 348, Pg. 339, 1996.
mouse LD50 intraperitoneal 179mg/kg (179mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Journal of Pharmacy and Pharmacology. Vol. 49, Pg. 1019, 1997.

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