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molecular formula C₂₇H₃₃D₆ClN₂O₄ B1140342 Verapamil-d6 Hydrochloride CAS No. 1185032-80-7

Verapamil-d6 Hydrochloride

Cat. No. B1140342
M. Wt: 497.1
InChI Key:
Attention: For research use only. Not for human or veterinary use.
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Patent
US06221335B1

Procedure details

Verapamil hydrochloride was added to a solution of 25% deuterated sulfuric acid in deuterated water (v/v) and deuterated methanol. The solution was stirred for 140 hours at 90° C. The pH was adjusted to 12.0 and the mixture extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water, dried over magnesium sulfate and evaporated to yield a viscous oil. This oil was dissolved in ether and ethereal hydrochloride was added to precipitate the hydrochloride salt. The salt was collected by filtration and crystallized from ethyl acetate to obtain deuterated verapamil as a white solid.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
deuterated sulfuric acid
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
[Compound]
Name
deuterated methanol
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH3:1][CH:2]([C:4]([C:24]1[CH:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)([C:22]#[N:23])[CH2:5][CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[CH3:9])[CH3:3].Cl.Cl>[2H]O[2H].CCOCC>[CH3:3][CH:2]([C:4]([C:24]1[CH:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)([C:22]#[N:23])[CH2:5][CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[CH3:9])[CH3:1] |f:0.1|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)C(CCCN(C)CCC=1C=CC(=C(C1)OC)OC)(C#N)C=2C=CC(=C(C2)OC)OC.Cl
Name
deuterated sulfuric acid
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
[2H]O[2H]
Name
deuterated methanol
Quantity
0 (± 1) mol
Type
solvent
Smiles
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl
Step Three
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CCOCC

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
90 °C
Stirring
Type
CUSTOM
Details
The solution was stirred for 140 hours at 90° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
the mixture extracted with ethyl acetate
WASH
Type
WASH
Details
The combined ethyl acetate extracts were washed with water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated
CUSTOM
Type
CUSTOM
Details
to yield a viscous oil
CUSTOM
Type
CUSTOM
Details
to precipitate the hydrochloride salt
FILTRATION
Type
FILTRATION
Details
The salt was collected by filtration
CUSTOM
Type
CUSTOM
Details
crystallized from ethyl acetate

Outcomes

Product
Details
Reaction Time
140 h
Name
Type
product
Smiles
CC(C)C(CCCN(C)CCC=1C=CC(=C(C1)OC)OC)(C#N)C=2C=CC(=C(C2)OC)OC

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
US06221335B1

Procedure details

Verapamil hydrochloride was added to a solution of 25% deuterated sulfuric acid in deuterated water (v/v) and deuterated methanol. The solution was stirred for 140 hours at 90° C. The pH was adjusted to 12.0 and the mixture extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water, dried over magnesium sulfate and evaporated to yield a viscous oil. This oil was dissolved in ether and ethereal hydrochloride was added to precipitate the hydrochloride salt. The salt was collected by filtration and crystallized from ethyl acetate to obtain deuterated verapamil as a white solid.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
deuterated sulfuric acid
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
[Compound]
Name
deuterated methanol
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH3:1][CH:2]([C:4]([C:24]1[CH:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)([C:22]#[N:23])[CH2:5][CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[CH3:9])[CH3:3].Cl.Cl>[2H]O[2H].CCOCC>[CH3:3][CH:2]([C:4]([C:24]1[CH:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)([C:22]#[N:23])[CH2:5][CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[CH3:9])[CH3:1] |f:0.1|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)C(CCCN(C)CCC=1C=CC(=C(C1)OC)OC)(C#N)C=2C=CC(=C(C2)OC)OC.Cl
Name
deuterated sulfuric acid
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
[2H]O[2H]
Name
deuterated methanol
Quantity
0 (± 1) mol
Type
solvent
Smiles
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl
Step Three
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CCOCC

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
90 °C
Stirring
Type
CUSTOM
Details
The solution was stirred for 140 hours at 90° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
the mixture extracted with ethyl acetate
WASH
Type
WASH
Details
The combined ethyl acetate extracts were washed with water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated
CUSTOM
Type
CUSTOM
Details
to yield a viscous oil
CUSTOM
Type
CUSTOM
Details
to precipitate the hydrochloride salt
FILTRATION
Type
FILTRATION
Details
The salt was collected by filtration
CUSTOM
Type
CUSTOM
Details
crystallized from ethyl acetate

Outcomes

Product
Details
Reaction Time
140 h
Name
Type
product
Smiles
CC(C)C(CCCN(C)CCC=1C=CC(=C(C1)OC)OC)(C#N)C=2C=CC(=C(C2)OC)OC

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
US06221335B1

Procedure details

Verapamil hydrochloride was added to a solution of 25% deuterated sulfuric acid in deuterated water (v/v) and deuterated methanol. The solution was stirred for 140 hours at 90° C. The pH was adjusted to 12.0 and the mixture extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water, dried over magnesium sulfate and evaporated to yield a viscous oil. This oil was dissolved in ether and ethereal hydrochloride was added to precipitate the hydrochloride salt. The salt was collected by filtration and crystallized from ethyl acetate to obtain deuterated verapamil as a white solid.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
deuterated sulfuric acid
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
[Compound]
Name
deuterated methanol
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH3:1][CH:2]([C:4]([C:24]1[CH:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)([C:22]#[N:23])[CH2:5][CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[CH3:9])[CH3:3].Cl.Cl>[2H]O[2H].CCOCC>[CH3:3][CH:2]([C:4]([C:24]1[CH:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)([C:22]#[N:23])[CH2:5][CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[CH3:9])[CH3:1] |f:0.1|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)C(CCCN(C)CCC=1C=CC(=C(C1)OC)OC)(C#N)C=2C=CC(=C(C2)OC)OC.Cl
Name
deuterated sulfuric acid
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
[2H]O[2H]
Name
deuterated methanol
Quantity
0 (± 1) mol
Type
solvent
Smiles
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl
Step Three
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CCOCC

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
90 °C
Stirring
Type
CUSTOM
Details
The solution was stirred for 140 hours at 90° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
the mixture extracted with ethyl acetate
WASH
Type
WASH
Details
The combined ethyl acetate extracts were washed with water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated
CUSTOM
Type
CUSTOM
Details
to yield a viscous oil
CUSTOM
Type
CUSTOM
Details
to precipitate the hydrochloride salt
FILTRATION
Type
FILTRATION
Details
The salt was collected by filtration
CUSTOM
Type
CUSTOM
Details
crystallized from ethyl acetate

Outcomes

Product
Details
Reaction Time
140 h
Name
Type
product
Smiles
CC(C)C(CCCN(C)CCC=1C=CC(=C(C1)OC)OC)(C#N)C=2C=CC(=C(C2)OC)OC

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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