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molecular formula C27H38N2O4 B1218737 Dexverapamil CAS No. 38321-02-7

Dexverapamil

Cat. No. B1218737
M. Wt: 454.6 g/mol
InChI Key: SGTNSNPWRIOYBX-HHHXNRCGSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08748648B2

Procedure details

In carrying out this synthesis, the following materials were used. Homovanillyl alcohol, Aldrich, 99%, Cat. No. 148830-10G, Batch No. 19516EO; potassium carbonate, Aldrich, 99%; triethylamine, Aldrich, 99.5%, Cat. No. 471283-500 mL, Batch No. 04623HD; methanesulfonyl chloride, Aldrich, 99.5%, Cat. No. 471259-500 mL, Batch No. 13209KC; 3,4-dimethoxyphenylacetonitrile, Aldrich, Cat. No. 126349-100G, Batch No. 08011BD; 2-iodopropane, Aldrich, 99%, Cat. No. 148938-100G, Batch #, 03604DD; diisopropylamine, redistilled, Aldrich, 99.95%, Cat. No. 386464-100 mL, Batch #00944TD; butyllithium, 1.6 M solution in hexanes, Aldrich, Cat. No. 186171-100 mL, Batch #20709PD; 3-bromo-1-propanol, Aldrich, 97%, Cat. No. 167169-25G, Batch No. 0901DE; dichloromethane, Aldrich, Cat. No. 270997-2L, Batch #: 00434 KD; sodium triacetoxyborohydride, Aldrich, 95%, Cat. No. 316393-25G, Batch No. 07920LD; N,N-diisopropylethylamine, Aldrich, Cat. No. 387649-100 mL, Batch No. 06448PC.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six

Identifiers

REACTION_CXSMILES
C(O)C[C:3]1[CH:11]=[CH:10][C:8](O)=[C:5]([O:6][CH3:7])[CH:4]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH3:19]S(Cl)(=O)=O.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:34][C:35]#[N:36])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].I[CH:38]([CH3:40])[CH3:39].[CH2:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])C>>[CH3:39][CH:38]([C:34]([C:28]1[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=1)([C:35]#[N:36])[CH2:19][CH2:45][CH2:44][N:43]([CH2:46][CH2:47][C:10]1[CH:11]=[CH:3][C:4]([O:16][CH3:13])=[C:5]([O:6][CH3:7])[CH:8]=1)[CH3:41])[CH3:40] |f:1.2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(CC1=CC(OC)=C(O)C=C1)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C([O-])([O-])=O.[K+].[K+]
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CS(=O)(=O)Cl
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
COC=1C=C(C=CC1OC)CC#N
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
IC(C)C
Step Six
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)N(CC)CC

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
this synthesis
DISTILLATION
Type
DISTILLATION
Details
diisopropylamine, redistilled

Outcomes

Product
Name
Type
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
US08748648B2

Procedure details

In carrying out this synthesis, the following materials were used. Homovanillyl alcohol, Aldrich, 99%, Cat. No. 148830-10G, Batch No. 19516EO; potassium carbonate, Aldrich, 99%; triethylamine, Aldrich, 99.5%, Cat. No. 471283-500 mL, Batch No. 04623HD; methanesulfonyl chloride, Aldrich, 99.5%, Cat. No. 471259-500 mL, Batch No. 13209KC; 3,4-dimethoxyphenylacetonitrile, Aldrich, Cat. No. 126349-100G, Batch No. 08011BD; 2-iodopropane, Aldrich, 99%, Cat. No. 148938-100G, Batch #, 03604DD; diisopropylamine, redistilled, Aldrich, 99.95%, Cat. No. 386464-100 mL, Batch #00944TD; butyllithium, 1.6 M solution in hexanes, Aldrich, Cat. No. 186171-100 mL, Batch #20709PD; 3-bromo-1-propanol, Aldrich, 97%, Cat. No. 167169-25G, Batch No. 0901DE; dichloromethane, Aldrich, Cat. No. 270997-2L, Batch #: 00434 KD; sodium triacetoxyborohydride, Aldrich, 95%, Cat. No. 316393-25G, Batch No. 07920LD; N,N-diisopropylethylamine, Aldrich, Cat. No. 387649-100 mL, Batch No. 06448PC.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six

Identifiers

REACTION_CXSMILES
C(O)C[C:3]1[CH:11]=[CH:10][C:8](O)=[C:5]([O:6][CH3:7])[CH:4]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH3:19]S(Cl)(=O)=O.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:34][C:35]#[N:36])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].I[CH:38]([CH3:40])[CH3:39].[CH2:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])C>>[CH3:39][CH:38]([C:34]([C:28]1[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=1)([C:35]#[N:36])[CH2:19][CH2:45][CH2:44][N:43]([CH2:46][CH2:47][C:10]1[CH:11]=[CH:3][C:4]([O:16][CH3:13])=[C:5]([O:6][CH3:7])[CH:8]=1)[CH3:41])[CH3:40] |f:1.2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(CC1=CC(OC)=C(O)C=C1)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C([O-])([O-])=O.[K+].[K+]
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CS(=O)(=O)Cl
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
COC=1C=C(C=CC1OC)CC#N
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
IC(C)C
Step Six
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)N(CC)CC

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
this synthesis
DISTILLATION
Type
DISTILLATION
Details
diisopropylamine, redistilled

Outcomes

Product
Name
Type
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
US08748648B2

Procedure details

In carrying out this synthesis, the following materials were used. Homovanillyl alcohol, Aldrich, 99%, Cat. No. 148830-10G, Batch No. 19516EO; potassium carbonate, Aldrich, 99%; triethylamine, Aldrich, 99.5%, Cat. No. 471283-500 mL, Batch No. 04623HD; methanesulfonyl chloride, Aldrich, 99.5%, Cat. No. 471259-500 mL, Batch No. 13209KC; 3,4-dimethoxyphenylacetonitrile, Aldrich, Cat. No. 126349-100G, Batch No. 08011BD; 2-iodopropane, Aldrich, 99%, Cat. No. 148938-100G, Batch #, 03604DD; diisopropylamine, redistilled, Aldrich, 99.95%, Cat. No. 386464-100 mL, Batch #00944TD; butyllithium, 1.6 M solution in hexanes, Aldrich, Cat. No. 186171-100 mL, Batch #20709PD; 3-bromo-1-propanol, Aldrich, 97%, Cat. No. 167169-25G, Batch No. 0901DE; dichloromethane, Aldrich, Cat. No. 270997-2L, Batch #: 00434 KD; sodium triacetoxyborohydride, Aldrich, 95%, Cat. No. 316393-25G, Batch No. 07920LD; N,N-diisopropylethylamine, Aldrich, Cat. No. 387649-100 mL, Batch No. 06448PC.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six

Identifiers

REACTION_CXSMILES
C(O)C[C:3]1[CH:11]=[CH:10][C:8](O)=[C:5]([O:6][CH3:7])[CH:4]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH3:19]S(Cl)(=O)=O.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:34][C:35]#[N:36])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].I[CH:38]([CH3:40])[CH3:39].[CH2:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])C>>[CH3:39][CH:38]([C:34]([C:28]1[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=1)([C:35]#[N:36])[CH2:19][CH2:45][CH2:44][N:43]([CH2:46][CH2:47][C:10]1[CH:11]=[CH:3][C:4]([O:16][CH3:13])=[C:5]([O:6][CH3:7])[CH:8]=1)[CH3:41])[CH3:40] |f:1.2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(CC1=CC(OC)=C(O)C=C1)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C([O-])([O-])=O.[K+].[K+]
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CS(=O)(=O)Cl
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
COC=1C=C(C=CC1OC)CC#N
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
IC(C)C
Step Six
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)N(CC)CC

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
this synthesis
DISTILLATION
Type
DISTILLATION
Details
diisopropylamine, redistilled

Outcomes

Product
Name
Type
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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