Product Name

  • Name

    Clomipramine

  • EINECS 206-144-2
  • CAS No. 303-49-1
  • Article Data120
  • CAS DataBase
  • Density 1.119 g/cm3
  • Solubility 25 mg/mL in water
  • Melting Point 189.5°C
  • Formula C19H23ClN2
  • Boiling Point 434.2 °C at 760 mmHg
  • Molecular Weight 314.858
  • Flash Point 216.4 °C
  • Transport Information
  • Appearance white to off-white powder
  • Safety 36
  • Risk Codes 20/21/22
  • Molecular Structure Molecular Structure of 303-49-1 (Clomipramine)
  • Hazard Symbols HarmfulXn
  • Synonyms 5H-Dibenz[b,f]azepine,3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro- (6CI,7CI,8CI);3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine;Chlorimipramine;G 34586;NSC 169865;
  • PSA 6.48000
  • LogP 4.59340

Synthetic route

clomipramine N-oxide
14171-67-6

clomipramine N-oxide

Clomipramine
303-49-1

Clomipramine

Conditions
ConditionsYield
With sodium tetrahydroborate In water at 50 - 60℃; chemoselective reaction;82%
3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine
32943-25-2

3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine

N,N-dimethyl-3-bromopropylamine
53929-74-1

N,N-dimethyl-3-bromopropylamine

Clomipramine
303-49-1

Clomipramine

Conditions
ConditionsYield
Stage #1: 3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine With sodium hydride In tetrahydrofuran at 110℃; for 2h; Glovebox; Inert atmosphere; Schlenk technique;
Stage #2: N,N-dimethyl-3-bromopropylamine In tetrahydrofuran at 110℃; for 22h; Glovebox; Inert atmosphere; Schlenk technique;		66%
3-chloro-5H-dibenzo[b,f]azepine
39607-90-4

3-chloro-5H-dibenzo[b,f]azepine

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

3-(Dimethylamino)propyl chloride

Clomipramine
303-49-1

Clomipramine

Conditions
ConditionsYield
Stage #1: 3-chloro-5H-dibenzo[b,f]azepine With methanol; magnesium at 50℃; for 1.5h;
Stage #2: 3-(Dimethylamino)propyl chloride
bromochlorobenzene
106-39-8

bromochlorobenzene

Clomipramine
303-49-1

Clomipramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate; triphenylphosphine; palladium diacetate; potassium iodide / N,N-dimethyl-formamide / 46 h / 105 °C / Schlenk technique; Inert atmosphere
2: N,N-dimethyl-formamide / 24 h / 130 °C / Schlenk technique; Inert atmosphere
3: magnesium; methanol / 1.5 h / 50 °C
View Scheme
2-bromoaniline
615-36-1

2-bromoaniline

Clomipramine
303-49-1

Clomipramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate; triphenylphosphine; palladium diacetate; potassium iodide / N,N-dimethyl-formamide / 46 h / 105 °C / Schlenk technique; Inert atmosphere
2: N,N-dimethyl-formamide / 24 h / 130 °C / Schlenk technique; Inert atmosphere
3: magnesium; methanol / 1.5 h / 50 °C
View Scheme
3-chloro-5-(3-dimethylaminopropyl)-10,11-dihydro-5H-dibenzo(6,5)azepine
25961-11-9

3-chloro-5-(3-dimethylaminopropyl)-10,11-dihydro-5H-dibenzo(6,5)azepine

Clomipramine
303-49-1

Clomipramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube
2.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube
3.1: sodium hydride / tetrahydrofuran / 2 h / 110 °C / Glovebox; Inert atmosphere; Schlenk technique
3.2: 22 h / 110 °C / Glovebox; Inert atmosphere; Schlenk technique
View Scheme
C20H23BClNO2

C20H23BClNO2

Clomipramine
303-49-1

Clomipramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube
2.1: sodium hydride / tetrahydrofuran / 2 h / 110 °C / Glovebox; Inert atmosphere; Schlenk technique
2.2: 22 h / 110 °C / Glovebox; Inert atmosphere; Schlenk technique
View Scheme
Clomipramine
303-49-1

Clomipramine

C19H13(2)H10ClN2

C19H13(2)H10ClN2

Conditions
ConditionsYield
Stage #1: Clomipramine With hydrogenchloride In 1,4-dioxane; ethyl acetate Inert atmosphere;
Stage #2: With 3,6-bis(dimethylamino)-9-(2,6-dimethylphenyl)-10-methylacridinium bromide; water-d2; lithium carbonate; triisopropylsilanethiol In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Inert atmosphere; Irradiation; regioselective reaction;		98%
2-(2-methylphenyl)pyridine
10273-89-9

2-(2-methylphenyl)pyridine

Clomipramine
303-49-1

Clomipramine

C31H33N3

C31H33N3

Conditions
ConditionsYield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 24h; Inert atmosphere;97%
Clomipramine
303-49-1

Clomipramine

C19H21(2)H2ClN2

C19H21(2)H2ClN2

Conditions
ConditionsYield
Stage #1: Clomipramine With hydrogenchloride In 1,4-dioxane; ethyl acetate Inert atmosphere;
Stage #2: With 9-(4-methoxyphenyl)-10-methylacridinium bromide; water-d2; lithium carbonate; triisopropylsilanethiol In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Inert atmosphere; Irradiation; regioselective reaction;		88%
Clomipramine
303-49-1

Clomipramine

tris-iso-propylsilyl acetylene
89343-06-6

tris-iso-propylsilyl acetylene

N,N-dimethyl-3-(3-((triisopropylsilyl)ethynyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

N,N-dimethyl-3-(3-((triisopropylsilyl)ethynyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

Conditions
ConditionsYield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate In acetonitrile at 85℃; for 7h; Sonogashira Cross-Coupling;87%
Clomipramine
303-49-1

Clomipramine

C19H15(2)H8ClN2

C19H15(2)H8ClN2

Conditions
ConditionsYield
Stage #1: Clomipramine With hydrogenchloride In 1,4-dioxane; ethyl acetate Inert atmosphere;
Stage #2: With 9-(4-fluorophenyl)-10-methylacridinium bromide; water-d2; lithium carbonate; triisopropylsilanethiol In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Inert atmosphere; Irradiation; regioselective reaction;		86%
Clomipramine
303-49-1

Clomipramine

3-(2,4-dibromo-7-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine

3-(2,4-dibromo-7-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine

Conditions
ConditionsYield
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃; for 5h;83%
Clomipramine
303-49-1

Clomipramine

C19H9(2)H14ClN2

C19H9(2)H14ClN2

Conditions
ConditionsYield
Stage #1: Clomipramine With hydrogenchloride In 1,4-dioxane; ethyl acetate Inert atmosphere;
Stage #2: With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; water-d2; lithium carbonate; triisopropylsilanethiol In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Inert atmosphere; Irradiation;		80%
Clomipramine
303-49-1

Clomipramine

3-(3-deuterio-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine
1610958-41-2

3-(3-deuterio-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; d8-isopropanol; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 100℃; for 2.5h; Inert atmosphere; Microwave irradiation;79%
Clomipramine
303-49-1

Clomipramine

C19H9(2)H14ClN2*ClH

C19H9(2)H14ClN2*ClH

Conditions
ConditionsYield
Stage #1: Clomipramine With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; water-d2; triisopropylsilanethiol In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Irradiation;
Stage #2: With hydrogenchloride In 1-methyl-pyrrolidin-2-one Irradiation;		76%
Clomipramine
303-49-1

Clomipramine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

C21H25N3

C21H25N3

Conditions
ConditionsYield
Stage #1: Clomipramine; ethyl 2-cyanoacetate With N-(2-methylnaphthalen-1-yl)-N’-(pyridin-2-ylmethyl)oxalamide; copper(I) bromide; sodium t-butanolate In isopropyl alcohol at 105℃; for 24h; Schlenk technique; Inert atmosphere;
Stage #2: With water In isopropyl alcohol at 105℃; for 12h; Schlenk technique; Inert atmosphere; Cooling;		72%
Clomipramine
303-49-1

Clomipramine

sodium trimethylsilyldimethylsilanolate

sodium trimethylsilyldimethylsilanolate

N,N-dimethyl-3-(3-trimethylsilyl-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propan-1-amine

N,N-dimethyl-3-(3-trimethylsilyl-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propan-1-amine

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); Dimethyl(phenyl)phosphine In toluene at 70℃; for 24h; Schlenk technique;69%
Clomipramine
303-49-1

Clomipramine

3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

N,N-dimethyl-3-(3-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

N,N-dimethyl-3-(3-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

Conditions
ConditionsYield
Stage #1: Clomipramine With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate In acetonitrile for 0.416667h; Sonogashira Cross-Coupling; Glovebox;
Stage #2: 3-(tetrahydropyran-2'-yloxy)propyne In acetonitrile at 80℃; for 20h; Sonogashira Cross-Coupling; Sealed tube;		63%
Clomipramine
303-49-1

Clomipramine

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

N,N-dimethyl-3-(3-(triethylsilyl)-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propan-1-amine

N,N-dimethyl-3-(3-(triethylsilyl)-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propan-1-amine

Conditions
ConditionsYield
With 3,4,7,8-Tetramethyl-o-phenanthrolin; ferrous iodide; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;54%
Clomipramine
303-49-1

Clomipramine

trimethyl(difluoromethyl)silane
65864-64-4

trimethyl(difluoromethyl)silane

3-(3-(difluoromethyl)-10,11-dihydro-5H-dibenzo[b,f ]-azepin-5-yl)-N,N-dimethylpropan-1-amine

3-(3-(difluoromethyl)-10,11-dihydro-5H-dibenzo[b,f ]-azepin-5-yl)-N,N-dimethylpropan-1-amine

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; cesium fluoride; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 16h; Reagent/catalyst; Glovebox; Sealed tube;48%
Clomipramine
303-49-1

Clomipramine

A

clomipramine N-oxide
14171-67-6

clomipramine N-oxide

B

impramine
50-49-7

impramine

C

3-hydroxyimipramine

3-hydroxyimipramine

D

3-hydroxyimipramine-N-oxide

3-hydroxyimipramine-N-oxide

Conditions
ConditionsYield
With oxygen In methanol; phosphate buffer at 25 - 28℃; pH=7.4; Product distribution; Further Variations:; Reagents; Photolysis; UV-irradiation;A 15%
B 15%
C 40%
D 20%
...Expand
Clomipramine
303-49-1

Clomipramine

desmethylclomipramine
303-48-0

desmethylclomipramine

Conditions
ConditionsYield
With oxygen; palladium on activated charcoal In methanol for 24h; Ambient temperature;
Clomipramine
303-49-1

Clomipramine

clomipramine N-oxide
14171-67-6

clomipramine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In methanol for 168h;
Clomipramine
303-49-1

Clomipramine

N,N-dimethyl-3-(3-(3-(2-(2-(naphthalene-1-yl)ethoxy)ethoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

N,N-dimethyl-3-(3-(3-(2-(2-(naphthalene-1-yl)ethoxy)ethoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere
View Scheme
Clomipramine
303-49-1

Clomipramine

N,N-dimethyl-3-(3-(3-(2-(2-(naphthalene-1-yloxy)ethoxy)ethoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

N,N-dimethyl-3-(3-(3-(2-(2-(naphthalene-1-yloxy)ethoxy)ethoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere
View Scheme
Clomipramine
303-49-1

Clomipramine

N,N-dimethyl-3-(3-(3-(2-(2-(naphthalene-1-ylthio)ethoxy)ethoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

N,N-dimethyl-3-(3-(3-(2-(2-(naphthalene-1-ylthio)ethoxy)ethoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere
View Scheme
Clomipramine
303-49-1

Clomipramine

3-(3-(3-(3-(10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)-N,N-dimethylpropane-1-amine

3-(3-(3-(3-(10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)-N,N-dimethylpropane-1-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere
View Scheme
Clomipramine
303-49-1

Clomipramine

3-(3-(3-(3-(3-(10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propoxy)propoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)-N,N-dimethylpropane-1-amine

3-(3-(3-(3-(3-(10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propoxy)propoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)-N,N-dimethylpropane-1-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere
View Scheme
Clomipramine
303-49-1

Clomipramine

N,N-dimethyl-3-(3-(3-(naphthalene-1-ylmethoxy)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

N,N-dimethyl-3-(3-(3-(naphthalene-1-ylmethoxy)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere
4.1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate
View Scheme
Clomipramine
303-49-1

Clomipramine

N,N-dimethyl-3-(3-(3-(2-(naphthalene-1-yloxy)ethoxy)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

N,N-dimethyl-3-(3-(3-(2-(naphthalene-1-yloxy)ethoxy)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere
4.1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate
View Scheme
Multi-step reaction with 4 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate
4.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere
View Scheme
Clomipramine
303-49-1

Clomipramine

N,N-dimethyl-3-(3-(3-(3-(naphthalene-1-yloxy)propoxy)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

N,N-dimethyl-3-(3-(3-(3-(naphthalene-1-yloxy)propoxy)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere
4.1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate
View Scheme
Multi-step reaction with 4 steps
1.1: chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / acetonitrile / 0.42 h / Glovebox
1.2: 20 h / 80 °C / Sealed tube
2.1: toluene-4-sulfonic acid / methanol / 2 h
3.1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate
4.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere
View Scheme

Clomipramine Chemical Properties

MF:  C19H23ClN2
MW:  314.85
MS:
EINECS: 206-144-2
Mol File: 303-49-1.mol
Solubility  H2O: 25 mg/mL
Form:  powder
color:  white to off-white
Surface Tension: 41.7 dyne/cm 
Density: 1.119 g/cm3 
Flash Point: 216.4 °C 
Enthalpy of Vaporization: 69.03 kJ/mol 
Boiling Point: 434.2 °C at 760 mmHg 
Vapour Pressure: 9.63E-08 mmHg at 25°C  
 

Clomipramine Uses

3-(9-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine hydrochloride (303-49-1 ) have effects on the performance of a variety of causes and symptoms of depression,Obsessive-compulsive disorder,associated with narcolepsy of cataplexy disorder, panic attacks, phobias, chronic pain state and nocturnal enuresis.
 

Clomipramine Toxicity Data With Reference

Organism

Test Type

Route

Reported Dose (Normalized Dose)

Effect

Source

man

TDLo

oral

357ug/kg (0.357mg/kg)

gastrointestinal: nausea or vomiting

Journal of Clinical Pyschopharmacology. Vol. 2, Pg. 215, 1982.

mouse

LD50

intraperitoneal

150mg/kg (150mg/kg)

 

Journal of Medicinal Chemistry. Vol. 21, Pg. 448, 1978.

mouse

LD50

intravenous

27mg/kg (27mg/kg)

 

Acta Pharmaceutica Suecica. Vol. 13, Pg. 485, 1976.

 

mouse

LD50

oral

380mg/kg (380mg/kg)

behavioral: wakefulness

behavioral: changes in motor activity (specific assay)

German Offenlegungsschrift Patent Document. Vol. #2618152,

rat

LD50

intraperitoneal

149mg/kg (149mg/kg)

 

Toxicology. Vol. 24, Pg. 335, 1982.

 

rat

LD50

oral

613mg/kg (613mg/kg)

 

Toxicology. Vol. 24, Pg. 335, 1982.

 

women

TDLo

intravenous

3400ug/kg/47M (3.4mg/kg)

behavioral: convulsions or effect on seizure threshold

cardiac: cardiomyopathy including infarction

British Medical Journal. Vol. 3, Pg. 698, 1972.

women

TDLo

oral

10mg/kg/5D-I (10mg/kg)

vascular: bp elevation not characterized in autonomic section

British Medical Journal. Vol. 1, Pg. 406, 1971.

women

TDLo

oral

30mg/kg (30mg/kg)

behavioral: coma

gastrointestinal: changes in structure or function of endocrine pancreas

gastrointestinal: decreased motility or constipation

Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 425, 1994

Clomipramine Safety Profile

Hazard Codes : Xn
Risk Statements:  20/21/22
20/21/22 : 3-(9-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine hydrochloride (303-49-1 ) is harmful by inhalation, in contact with skin and if swallowed .
Safety Statements : 36
36: Keep away from sources of ignition - No smoking
WGK Germany:  3
RTECS:  HN9055000
 
 

Clomipramine Specification

IUPAC Name: 3-(9-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine hydrochloride (303-49-1 )
CAS: 303-49-1
Synonyms: 3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine ; 3-Chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine ; 3-Chloroimipramine ; 5H-Dibenz(b,f)azepine, 10,11-dihydro-3-chloro-5-(3-(dimethylamino)propyl)- ; 5H-Dibenz[b,f]azepine, 3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro- ; 5H-Dibenz[b,f]azepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl- ; Anafranil (free base) ; Anafranil base
 

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