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molecular formula C16H25ClN2O B2978499 Ropinirole D3 Hydrochloride CAS No. 1329611-00-8

Ropinirole D3 Hydrochloride

Cat. No. B2978499
M. Wt: 299.86
InChI Key: XDXHAEQXIBQUEZ-NIIDSAIPSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US07619095B2

Procedure details

The process as shown above comprises conversion of 2-methyl-3-nitro phenyl acetic acid (II) with thionyl chloride to 2-Methyl-3-nitro-phenylacetyl chloride (III), which upon reaction with Di-n-propyl amine (DPA) gives 2-Methyl-3-nitro phenyl-N,N-di-n-propyl acetamide (IV) in syrup form. This intermediate (IV) is further reduced with Borane/THF and subsequent treatment with HCl/NaOH to give 2-Methyl-3-nitro phenyl ethyl-N,N-di-n-propyl amine (V). Further, compound (V) is treated with Na metal, Ethanol and diethyl oxalate to obtain Ethyl 6-(2-di-n-propylaminoethyl)-2-nitrophenyl pyruvate (VI), which is further treated with hydrogen peroxide , NaOH and HCl and converted to 6-(2-Di-n-propylaminoethyl)-2-nitro phenyl acetic acid hydrochloride (VII). This intermediate is reduced with palladium/carbon to give Ropinirole hydrochloride (Ia).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Three

Identifiers

REACTION_CXSMILES
OO.[OH-].[Na+].[ClH:5].Cl.[CH2:7]([N:10]([CH2:26][CH2:27][CH3:28])[CH2:11][CH2:12][C:13]1[C:18]([CH2:19][C:20](O)=[O:21])=[C:17]([N+:23]([O-])=O)[CH:16]=[CH:15][CH:14]=1)[CH2:8][CH3:9]>[Pd]>[CH3:9][CH2:8][CH2:7][N:10]([CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[NH:23][C:20](=[O:21])[CH2:19][C:18]=12)[CH2:26][CH2:27][CH3:28].[ClH:5] |f:1.2,4.5,7.8|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
OO
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl.C(CC)N(CCC1=CC=CC(=C1CC(=O)O)[N+](=O)[O-])CCC
Step Three
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pd]

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Outcomes

Product
Name
Type
product
Smiles
CCCN(CCC)CCC=1C=CC=C2C1CC(=O)N2.Cl

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US07619095B2

Procedure details

The process as shown above comprises conversion of 2-methyl-3-nitro phenyl acetic acid (II) with thionyl chloride to 2-Methyl-3-nitro-phenylacetyl chloride (III), which upon reaction with Di-n-propyl amine (DPA) gives 2-Methyl-3-nitro phenyl-N,N-di-n-propyl acetamide (IV) in syrup form. This intermediate (IV) is further reduced with Borane/THF and subsequent treatment with HCl/NaOH to give 2-Methyl-3-nitro phenyl ethyl-N,N-di-n-propyl amine (V). Further, compound (V) is treated with Na metal, Ethanol and diethyl oxalate to obtain Ethyl 6-(2-di-n-propylaminoethyl)-2-nitrophenyl pyruvate (VI), which is further treated with hydrogen peroxide , NaOH and HCl and converted to 6-(2-Di-n-propylaminoethyl)-2-nitro phenyl acetic acid hydrochloride (VII). This intermediate is reduced with palladium/carbon to give Ropinirole hydrochloride (Ia).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Three

Identifiers

REACTION_CXSMILES
OO.[OH-].[Na+].[ClH:5].Cl.[CH2:7]([N:10]([CH2:26][CH2:27][CH3:28])[CH2:11][CH2:12][C:13]1[C:18]([CH2:19][C:20](O)=[O:21])=[C:17]([N+:23]([O-])=O)[CH:16]=[CH:15][CH:14]=1)[CH2:8][CH3:9]>[Pd]>[CH3:9][CH2:8][CH2:7][N:10]([CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[NH:23][C:20](=[O:21])[CH2:19][C:18]=12)[CH2:26][CH2:27][CH3:28].[ClH:5] |f:1.2,4.5,7.8|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
OO
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl.C(CC)N(CCC1=CC=CC(=C1CC(=O)O)[N+](=O)[O-])CCC
Step Three
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pd]

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Outcomes

Product
Name
Type
product
Smiles
CCCN(CCC)CCC=1C=CC=C2C1CC(=O)N2.Cl

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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