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molecular formula C14H22N2O2 B1354846 (R)-Rivastigmine CAS No. 415973-05-6

(R)-Rivastigmine

Cat. No. B1354846
M. Wt: 250.34 g/mol
InChI Key: XSVMFMHYUFZWBK-LLVKDONJSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US07385076B2

Procedure details

The process of the present invention for example involves reacting 3-[1-(dimethylamino)ethyl]phenol with N-ethyl-N-methyl-4-nitrophenyl carbamate in the presence of potassium carbonate and dimethyl sulfoxide at a temperature ranging from about 80° C. to about 120° C. for about 30 to 40 hours, to form racemate of ethylmethylcarbamic acid 3-[1-(dimethylamino)ethyl]phenyl ester in the free base form. This racemate is then resolved to obtain the (S)-ethylmethylcarbamic acid 3-[1-(dimethylamino)ethyl]phenyl ester. The preferred method of resolution of the (S)-isomer from the racemate involves dissolving a mixture of the free base of the racemate and (+)-di-O, O′-p-toluoyl tartaric acid monohydrate in a 2:1 mixture of methanol:water by heating, collecting the precipitate on cooling by filtration, crystallizing the precipitate from a 2:1 mixture of ethanol:water, and obtaining the substantially pure (S)-isomer by partitioning it between 1N sodium hydroxide and a suitable organic solvent. The base may further be converted to its pharmaceutically acceptable acid addition salts, such as L(+)-tartrate salt.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
N-ethyl-N-methyl-4-nitrophenyl carbamate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]([CH3:12])[CH:3]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:4].[C:13](=[O:16])([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:12][N:2]([CH3:1])[CH:3]([C:5]1[CH:6]=[C:7]([O:11][C:13](=[O:16])[N:2]([CH2:3][CH3:4])[CH3:1])[CH:8]=[CH:9][CH:10]=1)[CH3:4] |f:1.2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN(C(C)C=1C=C(C=CC1)O)C
Step Two
Name
N-ethyl-N-methyl-4-nitrophenyl carbamate
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C([O-])([O-])=O.[K+].[K+]
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CS(=O)C

Conditions

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

Outcomes

Product
Details
Reaction Time
35 (± 5) h
Name
Type
product
Smiles
CN(C(C)C=1C=C(C=CC1)OC(N(C)CC)=O)C

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
US07385076B2

Procedure details

The process of the present invention for example involves reacting 3-[1-(dimethylamino)ethyl]phenol with N-ethyl-N-methyl-4-nitrophenyl carbamate in the presence of potassium carbonate and dimethyl sulfoxide at a temperature ranging from about 80° C. to about 120° C. for about 30 to 40 hours, to form racemate of ethylmethylcarbamic acid 3-[1-(dimethylamino)ethyl]phenyl ester in the free base form. This racemate is then resolved to obtain the (S)-ethylmethylcarbamic acid 3-[1-(dimethylamino)ethyl]phenyl ester. The preferred method of resolution of the (S)-isomer from the racemate involves dissolving a mixture of the free base of the racemate and (+)-di-O, O′-p-toluoyl tartaric acid monohydrate in a 2:1 mixture of methanol:water by heating, collecting the precipitate on cooling by filtration, crystallizing the precipitate from a 2:1 mixture of ethanol:water, and obtaining the substantially pure (S)-isomer by partitioning it between 1N sodium hydroxide and a suitable organic solvent. The base may further be converted to its pharmaceutically acceptable acid addition salts, such as L(+)-tartrate salt.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
N-ethyl-N-methyl-4-nitrophenyl carbamate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]([CH3:12])[CH:3]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:4].[C:13](=[O:16])([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:12][N:2]([CH3:1])[CH:3]([C:5]1[CH:6]=[C:7]([O:11][C:13](=[O:16])[N:2]([CH2:3][CH3:4])[CH3:1])[CH:8]=[CH:9][CH:10]=1)[CH3:4] |f:1.2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN(C(C)C=1C=C(C=CC1)O)C
Step Two
Name
N-ethyl-N-methyl-4-nitrophenyl carbamate
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C([O-])([O-])=O.[K+].[K+]
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CS(=O)C

Conditions

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

Outcomes

Product
Details
Reaction Time
35 (± 5) h
Name
Type
product
Smiles
CN(C(C)C=1C=C(C=CC1)OC(N(C)CC)=O)C

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
US07385076B2

Procedure details

The process of the present invention for example involves reacting 3-[1-(dimethylamino)ethyl]phenol with N-ethyl-N-methyl-4-nitrophenyl carbamate in the presence of potassium carbonate and dimethyl sulfoxide at a temperature ranging from about 80° C. to about 120° C. for about 30 to 40 hours, to form racemate of ethylmethylcarbamic acid 3-[1-(dimethylamino)ethyl]phenyl ester in the free base form. This racemate is then resolved to obtain the (S)-ethylmethylcarbamic acid 3-[1-(dimethylamino)ethyl]phenyl ester. The preferred method of resolution of the (S)-isomer from the racemate involves dissolving a mixture of the free base of the racemate and (+)-di-O, O′-p-toluoyl tartaric acid monohydrate in a 2:1 mixture of methanol:water by heating, collecting the precipitate on cooling by filtration, crystallizing the precipitate from a 2:1 mixture of ethanol:water, and obtaining the substantially pure (S)-isomer by partitioning it between 1N sodium hydroxide and a suitable organic solvent. The base may further be converted to its pharmaceutically acceptable acid addition salts, such as L(+)-tartrate salt.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
N-ethyl-N-methyl-4-nitrophenyl carbamate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]([CH3:12])[CH:3]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:4].[C:13](=[O:16])([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:12][N:2]([CH3:1])[CH:3]([C:5]1[CH:6]=[C:7]([O:11][C:13](=[O:16])[N:2]([CH2:3][CH3:4])[CH3:1])[CH:8]=[CH:9][CH:10]=1)[CH3:4] |f:1.2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN(C(C)C=1C=C(C=CC1)O)C
Step Two
Name
N-ethyl-N-methyl-4-nitrophenyl carbamate
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C([O-])([O-])=O.[K+].[K+]
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CS(=O)C

Conditions

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

Outcomes

Product
Details
Reaction Time
35 (± 5) h
Name
Type
product
Smiles
CN(C(C)C=1C=C(C=CC1)OC(N(C)CC)=O)C

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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