Product Name

  • Name

    Rimonabant hydrochloride

  • EINECS 233-720-0
  • CAS No. 158681-13-1
  • Article Data12
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 230-240 °C
  • Formula C22H21Cl3N4O.HCl
  • Boiling Point 627.6 °C at 760 mmHg
  • Molecular Weight 500.255
  • Flash Point 333.3 °C
  • Transport Information
  • Appearance White to Off-White Crystalline Solid
  • Safety 26-45
  • Risk Codes 25-36
  • Molecular Structure Molecular Structure of 158681-13-1 (Rimonabant hydrochloride)
  • Hazard Symbols T,Xi
  • Synonyms 1H-Pyrazole-3-carboxamide,5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-,monohydrochloride (9CI);5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide hydrochloride (1:1);Ribafit;Riomont;N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochloride;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide monohydrochloride;
  • PSA 50.16000
  • LogP 7.06940

Synthetic route

N-aminopiperidine hydrochloride
63234-70-8

N-aminopiperidine hydrochloride

rimonabant acid
162758-35-2

rimonabant acid

rimonabant
168273-06-1

rimonabant

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Stage #1: rimonabant acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 6h;
Stage #2: N-aminopiperidine hydrochloride With triethylamine In tetrahydrofuran at 60℃; for 1.5h;
Stage #3: rimonabant With hydrogenchloride		92.7%
...Expand
1-Aminopiperidine
2213-43-6

1-Aminopiperidine

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride
168273-05-0

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Stage #1: 1-Aminopiperidine; 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 10 - 25℃; for 2 - 3.5h;
Stage #2: With hydrogenchloride In water; acetone at 20 - 25℃; for 0.5h;
Stage #1: 1-Aminopiperidine; 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride With triethylamine In dichloromethane at 10 - 20℃; for 1h;
Stage #2: With hydrogenchloride pH=1;		33 g
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
2: hydrogenchloride / diethyl ether / pH 1
View Scheme
With TEA In dichloromethane at 0 - 20℃; for 0.5h;
rimonabant
168273-06-1

rimonabant

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20℃;
With hydrogenchloride In water; acetone at 0 - 55℃; for 0.25 - 1.25h; Product distribution / selectivity;
With hydrogenchloride In methanol; butyl methyl ether at 20℃; for 2h; pH=1.0;
4'-chloropropiophenone
6285-05-8

4'-chloropropiophenone

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine; methyl iodide / acetonitrile / 24 h / 20 - 45 °C / Inert atmosphere
2.1: tetrahydrofuran / 5 h / 10 - 20 °C
3.1: triethylamine / toluene / 12 h / 20 °C
4.1: toluene-4-sulfonic acid / toluene / 12 h / Reflux
5.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C / Cooling with ice
6.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
6.2: pH 1
View Scheme
C17H13Cl3N2O3

C17H13Cl3N2O3

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / toluene / 12 h / Reflux
2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C / Cooling with ice
3.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
3.2: pH 1
View Scheme
2,4-dichlorophenyl hydrazine hydrochloride
5446-18-4

2,4-dichlorophenyl hydrazine hydrochloride

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / toluene / 12 h / 20 °C
2.1: toluene-4-sulfonic acid / toluene / 12 h / Reflux
3.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C / Cooling with ice
4.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
4.2: pH 1
View Scheme
Multi-step reaction with 3 steps
2.1: propionic acid / 16 h / Heating / reflux
2.2: 20 h / 140 - 145 °C
3.1: hydrogenchloride / water; isopropyl alcohol / 9.08 h / 10 - 20 °C
View Scheme
5-(4-chlorophenyl)-4-methyl-2,3-furandione

5-(4-chlorophenyl)-4-methyl-2,3-furandione

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / toluene / 12 h / 20 °C
2.1: toluene-4-sulfonic acid / toluene / 12 h / Reflux
3.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C / Cooling with ice
4.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
4.2: pH 1
View Scheme
[[1-(4-chlorophenyl)-1-propenyl]oxy]trimethylsilane

[[1-(4-chlorophenyl)-1-propenyl]oxy]trimethylsilane

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 5 h / 10 - 20 °C
2.1: triethylamine / toluene / 12 h / 20 °C
3.1: toluene-4-sulfonic acid / toluene / 12 h / Reflux
4.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C / Cooling with ice
5.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
5.2: pH 1
View Scheme
4-(4-chlorophenyl)-3-methyl-2,4-dioxobutyric acid ethyl ester
169544-41-6

4-(4-chlorophenyl)-3-methyl-2,4-dioxobutyric acid ethyl ester

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2.1: propionic acid / 16 h / Heating / reflux
2.2: 20 h / 140 - 145 °C
3.1: hydrogenchloride / water; isopropyl alcohol / 9.08 h / 10 - 20 °C
View Scheme
rimonabant acid
162758-35-2

rimonabant acid

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / toluene / 3 h / Heating / reflux
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C
3: hydrogenchloride / diethyl ether / pH 1
View Scheme
ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate
158941-22-1

ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide; water / methanol / 3 h / Heating / reflux
2: thionyl chloride / toluene / 3 h / Heating / reflux
3: triethylamine / dichloromethane / 3 h / 0 - 20 °C
4: hydrogenchloride / diethyl ether / pH 1
View Scheme
rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

rimonabant
168273-06-1

rimonabant

Conditions
ConditionsYield
With methanol; potassium hydroxide; water at 0 - 5℃; for 1h;93%
With sodium hydroxide In methanol; water pH=8.5;
With sodium hydroxide In methanol; water at 28 - 30℃; for 0.666667h; pH=11;
rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

rimonabant hydrochloride ethanolate
1000380-28-8

rimonabant hydrochloride ethanolate

Conditions
ConditionsYield
In ethanol Product distribution / selectivity; Heating / reflux;
rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

rimonabant hydrochloride dichloromethanate

rimonabant hydrochloride dichloromethanate

Conditions
ConditionsYield
In dichloromethane Product distribution / selectivity; Heating / reflux;
rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

rimonabant hydrochloride hemi-isopropanolate

rimonabant hydrochloride hemi-isopropanolate

Conditions
ConditionsYield
In isopropyl alcohol Product distribution / selectivity; Heating / reflux;
In tetrahydrofuran; ethyl acetate; isopropyl alcohol Product distribution / selectivity; Heating / reflux;
rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)pyrazole-3-carboxamide hydrate
945634-91-3

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)pyrazole-3-carboxamide hydrate

Conditions
ConditionsYield
With ammonia; water In methanol at 25 - 30℃; for 2h; pH=8.0 - 10.0; Product distribution / selectivity;
With water In methanol at -14 - 45℃; for 0.666667h; Product distribution / selectivity;
With water In methanol at 20 - 60℃; under 390.039 Torr; for 12h; Product distribution / selectivity; Heating / reflux;
methanol
67-56-1

methanol

rimonabant hydrochloride
158681-13-1

rimonabant hydrochloride

A

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)pyrazole-3-carboxamide hydrate
945634-91-3

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)pyrazole-3-carboxamide hydrate

B

rimonabant methanol solvate

rimonabant methanol solvate

Conditions
ConditionsYield
With water at 20℃; for 72h; Product distribution / selectivity; Heating / reflux;
...Expand

Rimonabant hydrochloride Specification

The Rimonabant hydrochloride, with the CAS registry number 158681-13-1, is also known as 1H-Pyrazole-3-carboxamide,5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-,hydrochloride (1:1). It belongs to the product categories of API; Cnbio; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Aromatics; Heterocycles. This chemical's molecular formula is C22H21Cl3N4O.HCl and molecular weight is 500.25. What's more, its systematic name is 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide hydrochloride (1:1). Its classification code is Anti-Obesity Agents. This chemical is a potent & selective antagonist of the brain cannabinoid receptor.

Physical properties of Rimonabant hydrochloride are: (1)ACD/LogP: 6.138; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.14; (4)ACD/LogD (pH 7.4): 6.14; (5)ACD/BCF (pH 5.5): 27061.60; (6)ACD/BCF (pH 7.4): 27198.54; (7)ACD/KOC (pH 5.5): 51715.72; (8)ACD/KOC (pH 7.4): 51977.41; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 41.37 Å2; (13)Flash Point: 333.3 °C; (14)Enthalpy of Vaporization: 94.57 kJ/mol; (15)Boiling Point: 627.6 °C at 760 mmHg; (16)Vapour Pressure: 5.29E-16 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NN1CCCCC1)c4nn(c2ccc(Cl)cc2Cl)c(c3ccc(Cl)cc3)c4C.Cl
(2)Std. InChI: InChI=1S/C22H21Cl3N4O.ClH/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15;/h5-10,13H,2-4,11-12H2,1H3,(H,27,30);1H
(3)Std. InChIKey: REOYOKXLUFHOBV-UHFFFAOYSA-N

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