5763-44-0

Basic information

• Product Name: Cyclopentane-1,2-dicarboximude
• Synonyms: CYCLOPENTANE O-DICARBOXYLICIMIDE;CYCLOPENTANE-1,2-DICARBOXIMIDE;tetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione;1,2-Cyclopentane Dicarboximide;SODIUM ACETATE TRIHYDRATE BP ACS USP;4,5,6,6a-Tetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione;4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione;4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-quinone
• CAS NO: 5763-44-0
• Molecular Formula: C₇H₉NO₂
• Molecular Weight: 139.15
• EINECS: 240-071-7
• Product Categories: Pharmaceutical Intermediates
• Mol File: 5763-44-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 168 °C (dec.)
• Boiling Point: 322.2°C at 760 mmHg
• Flash Point: 162.2°C
• Appearance: /
• Density: 1.242g/cm³
• Vapor Pressure: 0.000283mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 11.97±0.20(Predicted)
• CAS DataBase Reference: Cyclopentane-1,2-dicarboximude(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentane-1,2-dicarboximude(5763-44-0)
• EPA Substance Registry System: Cyclopentane-1,2-dicarboximude(5763-44-0)

Safety Data

• Hazardous Substances Data: 5763-44-0(Hazardous Substances Data)

Usage

Uses

1,2-Cyclopentanedicarboximide was used as a reactant for [(benzopyranyl)amino]alkyl]azabicyclooctanedione anxiolytic,

InChI:InChI=1/C7H9NO2/c9-6-4-2-1-3-5(4)7(10)8-6/h4-5H,1-3H2,(H,8,9,10)

Synthetic route

diethyl cyclopentane-1,2-dicarboxylate (90474-13-8) → 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0)

Conditions	Yield
With ammonia at 130 - 280℃; for 5h; Product distribution / selectivity; autoclave; Pyrolysis; Industry scale;	96%

trans-DL-1,2-cyclopentanedicarboxylic acid (50483-99-3) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0)

Conditions	Yield
at 170℃; Temperature; Inert atmosphere;	93.5%

cyclopentane-1,2-dicarboxamide + 2-carbamylcyclopentane-1-carboxylic acid → 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0)

Conditions	Yield
In diphenylether at 240℃; for 2.5h; Temperature; Inert atmosphere; Industrial scale;	92.6%

cyclopentane-dicarboxylic acid-(1.2)-anhydride → 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0)

Conditions	Yield
With ammonia at 180℃;

C13H20N2O → 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / toluene; water / 4 h / 120 °C 2: chlorine / 1,2-dichloro-ethane / 10 h / -10 - 0 °C 3: ammonium hydroxide / 5 h / -10 - 0 °C 4: trans-DL-1,2-cyclopentanedicarboxylic acid / 2 h / 220 - 240 °C View Scheme

cyclohexanone-2-carboxamide (22945-27-3) → 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorine / 1,2-dichloro-ethane / 10 h / -10 - 0 °C 2: ammonium hydroxide / 5 h / -10 - 0 °C 3: trans-DL-1,2-cyclopentanedicarboxylic acid / 2 h / 220 - 240 °C View Scheme

cyclopentane-1,2-dicarboxamide → 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0)

Conditions	Yield
With trans-DL-1,2-cyclopentanedicarboxylic acid at 220 - 240℃; for 2h;

4-chlorobutyl bromide (6940-78-9) + 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → 2-(4-chlorobutyl)tetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	98%

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) + tert-butyl 4-[4-chloro-2-[2-(hydroxymethyl)thieno[3,2-b]pyridin-7-yl]-6-methyl-phenoxy]piperidine-1-carboxylate → tert-butyl 4-(4-chloro-2-(2-((1,3-dioxohexahydrocyclopenta[c]pyrrol-2(1H)-yl)methyl)thieno[3,2-b]pyridin-7-yl)-6-methylphenoxy)piperidine-1-carboxylate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 60℃; for 2h; Mitsunobu Displacement;	69%

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → C7H8ClNO2

Conditions	Yield
With trichloroisocyanuric acid In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique;	64%

1,4-dibromo-butane (110-52-1) + 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → N-(4-bromobutyl)-2,4-dioxo-3-azabicyclo [3.3.0]octane (138278-16-7)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 60℃; for 6h;	58%

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) + sulfate solution → lactam of/the/ 2-aminomethyl-cyclopentane-carboxylic acid-(1)

Conditions	Yield
at 0 - 5℃; elektrolytische Reduktion;

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → 3-[4-[N-(5-Methoxychroman-3-Yl)Amino]Butyl]-2,4-Dioxo-3-Azabicyclo[3.3.0]Octane (138277-79-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 58 percent / KI, K2CO3 / acetonitrile / 6 h / 60 °C 2: 66 percent / triethylamine, KI / dimethylformamide / 24 h / 60 °C View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → 3-{4-[N-PROPYL-N-(5-METHOXY-3-CHROMANYL)AMINO]-BUTYL}-2,4-DIOXO-3-AZABICYCLO[3.3.0]OCTANE

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / KI, K2CO3 / acetonitrile / 6 h / 60 °C 2: 66 percent / triethylamine, KI / dimethylformamide / 24 h / 60 °C 3: 78 percent / K2CO3 / dimethylformamide / 24 h / 60 °C View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → cis-octahydrocyclopenta[c]pyrrole

Conditions	Yield
With hydrogen; copper chromite In 1,4-dioxane at 265℃; under 153765 Torr; Product distribution / selectivity; Industry scale;

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → cis-octahydrocyclopenta[c]pyrrole hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / copper chromite / 1,4-dioxane / 265 °C / 153765 Torr / Industry scale 2: ethanol; water / 0.5 h / 0 - 20 °C View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1H)-yl]propoxy}benzamide hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen / copper chromite / 1,4-dioxane / 265 °C / 153765 Torr / Industry scale 2.1: ethanol; water / 0.5 h / 0 - 20 °C 3.1: trimethyl orthoformate; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.83 h / 40 °C 3.3: 40 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogen / copper chromite / 1,4-dioxane / 265 °C / 153765 Torr / Industry scale 2: triethylamine / isopropyl alcohol; water / Industry scale; Reflux 3: hydrogenchloride / water / 2.5 h / 20 - 60 °C / Industry scale View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1H)-yl]propoxy}benzamide

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / copper chromite / 1,4-dioxane / 265 °C / 153765 Torr / Industry scale 2: triethylamine / isopropyl alcohol; water / Industry scale; Reflux View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → hexahydrocyclopenta[c]pyrrole-1(2H)-one (56593-76-1)

Conditions	Yield
With hexarhodium hexadecacarbonyl; hydrogen; molybdenum hexacarbonyl In 2-methyltetrahydrofuran at 160℃; under 75007.5 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Pressure; Autoclave; Inert atmosphere;	94 %Chromat.

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → octahydrocyclopenta[c]pyrrole (1468-87-7, 5661-03-0, 10268-00-5) + hexahydrocyclopenta[c]pyrrole-1(2H)-one (56593-76-1)

Conditions	Yield
With hexarhodium hexadecacarbonyl; hydrogen; molybdenum hexacarbonyl In 1,4-dioxane at 160℃; under 75007.5 Torr; for 15h; Autoclave; Inert atmosphere;	A 71 %Chromat. B 14 %Chromat.
With hydrogen; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 160℃; under 75007.5 Torr; for 48h; Reagent/catalyst; Autoclave; Inert atmosphere;	A 48 %Chromat. B 52 %Chromat.

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → octahydrocyclopenta[c]pyrrole (1468-87-7, 5661-03-0, 10268-00-5)

Conditions	Yield
With hexarhodium hexadecacarbonyl; hydrogen; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 160℃; under 75007.5 Torr; for 24h; Reagent/catalyst; Autoclave; Inert atmosphere;	100 %Chromat.

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → 2-(4-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)butyl)tetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 12 h / 95 °C 2.2: 0.5 h View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) + 1-bromo-2-cyclopropylbenzene (57807-28-0) → 3-(2-cyclopropylphenyl)hexahydrocyclopenta[c]pyrrol-1(2H)-one

Conditions	Yield
Stage #1: 1-bromo-2-cyclopropylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; sodium cyanoborohydride In tetrahydrofuran; hexane; water at 0 - 20℃; for 1h; Inert atmosphere;	2.8 g

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) + C12H11FO2 → C19H20FNO4 + C19H20FNO4

Conditions	Yield
With 2,6-dibromophenol; C21H23F5NOPS In toluene at 0℃; Overall yield = 86 percent;	A n/a B n/a

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → C13H15NO

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Cooling with ice 2: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 1 h / 50 °C View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → C19H19NO

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Cooling with ice 2: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 1 h / 50 °C 3: copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 8 h / 100 °C / Inert atmosphere View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → C19H18N2O3

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Cooling with ice 2: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 1 h / 50 °C 3: copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 8 h / 100 °C / Inert atmosphere View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → C13H14ClNO

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Cooling with ice 2: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 1 h / 50 °C View Scheme

4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → C19H18ClNO

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Cooling with ice 2: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 1 h / 50 °C 3: copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 8 h / 100 °C / Inert atmosphere View Scheme

Upstream product

• 714192-66-2 2-carbamylcyclopentane-1-carboxylic acid 
• 22945-27-3 cyclohexanone-2-carboxamide 
• 50483-99-3 trans-DL-1,2-cyclopentanedicarboxylic acid 
• 77287-34-4 formamide 
• 90474-13-8 diethyl cyclopentane-1,2-dicarboxylate 

Downstream Products

• 1050666-51-7 N-amino-1,2-cyclopentanedicarboximide 
• 1468-87-7 octahydrocyclopenta[c]pyrrole 
• 56593-76-1 hexahydrocyclopenta[c]pyrrole-1(2H)-one 
• 1222097-72-4 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1H)-yl]propoxy}benzamide hydrochloride 

Relevant articles and documents

Synthesis process of N-amino-3-azabicyclo [3, 3, 0] octane hydrochloride

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The invention discloses a synthesis method of cyclopentane-1,2-dicarboximide. The synthesis method comprises the following steps: performing dehydration on cyclohexanone and urea as raw materials under the actions of a polymerization inhibitor and a water-carrying agent, heating, dropwise adding an acid liquor for hydrolyzing, adding an alcoholic solvent in the hydrolyzed solution, crystallizing,centrifuging, and drying to obtain cyclohexane-2-carboxamide, dissolving cyclohexane-2-carboxamide in halogenated hydrocarbon, performing halogenation under a halogenation reagent, performing cooling,crystallizing, hydrolyzing, centrifuging and drying to obtain a halide, dispersing the halide in an ammoniating solution for Favorskii rearrangement, sequentially performing cooling, crystallizing, centrifuging, washing and drying to obtain a rearrangement object, namely cyclopentane-1,2-carboxamide, finally adding a proper amount of catalysts, and after high temperature cyclization, performing reduced pressure distillation, performing refined crystallization, centrifuging, and drying, thereby obtaining cyclopentane-1,2-dicarboximide. The synthesis method has the advantages that the reactionstep is shortened, the environmental protection is benefited, the production cost is reduced, and the synthesis method is suitable for large-scale mass production.

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