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molecular formula C20H25ClN2O5 B1678800 (R)-Amlodipine CAS No. 103129-81-3

(R)-Amlodipine

Cat. No. B1678800
M. Wt: 408.9 g/mol
InChI Key: HTIQEAQVCYTUBX-QGZVFWFLSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US06846932B1

Procedure details

To a stirred solution of 100 gm (0.245 moles) of RS amlodipine in 150 ml DMSO was added a solution of 9.2 gm (0.06 moles, 0.25 eq) of L (+) tartaric acid in 100 ml DMSO. The solid starts separating from clear solution within 5-10 mins. This was stirred for 3 hrs and solid was filtered off, washed with acetone and dried to give 58.6 gm (40.5%) R (+) amlodipine hemi L(+) tartarate mono DMSO solvate. mp. 160-162° C., 96.8% d.e. by chiral HPLC.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
150 mL
Type
solvent
Reaction Step One
Name
Quantity
100 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([OH:38])(=[O:37])[CH:30]([CH:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31]>CS(C)=O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[C@H:11]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([O-:38])(=[O:37])[C@@H:30]([C@H:32]([C:34]([O-:36])=[O:35])[OH:33])[OH:31]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CCOC(=O)C1=C(NC(=C(C1C=2C=CC=CC2Cl)C(=O)OC)C)COCCN
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(O)C(O)C(=O)O)(=O)O
Name
Quantity
150 mL
Type
solvent
Smiles
CS(=O)C
Name
Quantity
100 mL
Type
solvent
Smiles
CS(=O)C

Conditions

Stirring
Type
CUSTOM
Details
This was stirred for 3 hrs
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
The solid starts separating from clear solution within 5-10 mins
Duration
7.5 (± 2.5) min
FILTRATION
Type
FILTRATION
Details
solid was filtered off
WASH
Type
WASH
Details
washed with acetone
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
3 h
Name
Type
product
Smiles
CCOC(=O)C1=C(NC(=C([C@H]1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
Name
Type
product
Smiles
C([C@H](O)[C@@H](O)C(=O)[O-])(=O)[O-]

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
US06846932B1

Procedure details

To a stirred solution of 100 gm (0.245 moles) of RS amlodipine in 150 ml DMSO was added a solution of 9.2 gm (0.06 moles, 0.25 eq) of L (+) tartaric acid in 100 ml DMSO. The solid starts separating from clear solution within 5-10 mins. This was stirred for 3 hrs and solid was filtered off, washed with acetone and dried to give 58.6 gm (40.5%) R (+) amlodipine hemi L(+) tartarate mono DMSO solvate. mp. 160-162° C., 96.8% d.e. by chiral HPLC.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
150 mL
Type
solvent
Reaction Step One
Name
Quantity
100 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([OH:38])(=[O:37])[CH:30]([CH:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31]>CS(C)=O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[C@H:11]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([O-:38])(=[O:37])[C@@H:30]([C@H:32]([C:34]([O-:36])=[O:35])[OH:33])[OH:31]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CCOC(=O)C1=C(NC(=C(C1C=2C=CC=CC2Cl)C(=O)OC)C)COCCN
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(O)C(O)C(=O)O)(=O)O
Name
Quantity
150 mL
Type
solvent
Smiles
CS(=O)C
Name
Quantity
100 mL
Type
solvent
Smiles
CS(=O)C

Conditions

Stirring
Type
CUSTOM
Details
This was stirred for 3 hrs
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
The solid starts separating from clear solution within 5-10 mins
Duration
7.5 (± 2.5) min
FILTRATION
Type
FILTRATION
Details
solid was filtered off
WASH
Type
WASH
Details
washed with acetone
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
3 h
Name
Type
product
Smiles
CCOC(=O)C1=C(NC(=C([C@H]1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
Name
Type
product
Smiles
C([C@H](O)[C@@H](O)C(=O)[O-])(=O)[O-]

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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