Amlodipine besylate
Katalognummer B192989
Molekulargewicht: 567.1 g/mol
InChI-Schlüssel: ZPBWCRDSRKPIDG-UHFFFAOYSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
Patent
US06887886B2
Procedure details
To a slight suspension of racemic amlodipine besylate (100.37 g, 0.177 mol) [prepared by the method described in European Patent No. 0244944] in methylene chloride (250 mL, 2.5 mL/g) and water (250 mL, 2.5 mL/g) was added 11 M sodium hydroxide (24 mL) to achieve pH 13-14. The mixture was stirred for ten minutes during which time it became a solution. The layers were separated and the organic layer washed with water (1×250 mL) and gravity filtered through a magnesium sulphate (25 g) bed. The magnesium sulphate was washed with methylene chloride (40 mL) and to the combined filtrates was added dimethyl sulphoxide (360 mL). The methylene chloride was removed on a rotary evaporator (45 minutes on a water aspirator followed by 15 minutes under high vacuum).
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].C1C=CC(S(O)(=O)=O)=CC=1.O.[OH-].[Na+]>C(Cl)Cl>[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH: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] |f:0.1,3.4|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
100.37 g
|
|
Type
|
reactant
|
|
Smiles
|
CCOC(=O)C1=C(NC(=C(C1C=2C=CC=CC2Cl)C(=O)OC)C)COCCN.C=1C=CC(=CC1)S(=O)(=O)O
|
Step Two
|
Name
|
|
|
Quantity
|
250 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
|
Name
|
|
|
Quantity
|
24 mL
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[Na+]
|
|
Name
|
|
|
Quantity
|
250 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(Cl)Cl
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
The mixture was stirred for ten minutes during which time it
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
prepared by the method
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The layers were separated
|
WASH
|
Type
|
WASH
|
|
Details
|
the organic layer washed with water (1×250 mL) and gravity
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered through a magnesium sulphate (25 g) bed
|
WASH
|
Type
|
WASH
|
|
Details
|
The magnesium sulphate was washed with methylene chloride (40 mL) and to the combined filtrates
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
was added dimethyl sulphoxide (360 mL)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The methylene chloride was removed on a rotary evaporator (45 minutes on a water
|
|
Duration
|
45 min
|
Outcomes
Product
Details
Reaction Time |
15 min |
|
Name
|
|
|
Type
|
|
|
Smiles
|
CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
|
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
US06887886B2
Procedure details
To a slight suspension of racemic amlodipine besylate (100.37 g, 0.177 mol) [prepared by the method described in European Patent No. 0244944] in methylene chloride (250 mL, 2.5 mL/g) and water (250 mL, 2.5 mL/g) was added 11 M sodium hydroxide (24 mL) to achieve pH 13-14. The mixture was stirred for ten minutes during which time it became a solution. The layers were separated and the organic layer washed with water (1×250 mL) and gravity filtered through a magnesium sulphate (25 g) bed. The magnesium sulphate was washed with methylene chloride (40 mL) and to the combined filtrates was added dimethyl sulphoxide (360 mL). The methylene chloride was removed on a rotary evaporator (45 minutes on a water aspirator followed by 15 minutes under high vacuum).
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].C1C=CC(S(O)(=O)=O)=CC=1.O.[OH-].[Na+]>C(Cl)Cl>[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH: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] |f:0.1,3.4|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
100.37 g
|
|
Type
|
reactant
|
|
Smiles
|
CCOC(=O)C1=C(NC(=C(C1C=2C=CC=CC2Cl)C(=O)OC)C)COCCN.C=1C=CC(=CC1)S(=O)(=O)O
|
Step Two
|
Name
|
|
|
Quantity
|
250 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
|
Name
|
|
|
Quantity
|
24 mL
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[Na+]
|
|
Name
|
|
|
Quantity
|
250 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(Cl)Cl
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
The mixture was stirred for ten minutes during which time it
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
prepared by the method
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The layers were separated
|
WASH
|
Type
|
WASH
|
|
Details
|
the organic layer washed with water (1×250 mL) and gravity
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered through a magnesium sulphate (25 g) bed
|
WASH
|
Type
|
WASH
|
|
Details
|
The magnesium sulphate was washed with methylene chloride (40 mL) and to the combined filtrates
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
was added dimethyl sulphoxide (360 mL)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The methylene chloride was removed on a rotary evaporator (45 minutes on a water
|
|
Duration
|
45 min
|
Outcomes
Product
Details
Reaction Time |
15 min |
|
Name
|
|
|
Type
|
|
|
Smiles
|
CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
|
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. |
