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molecular formula C23H27FN4O2 B2424515 Risperidone-D5 CAS No. 1225444-63-2

Risperidone-D5

Cat. No. B2424515
M. Wt: 415.524
InChI Key: RAPZEAPATHNIPO-SGEUAGPISA-N
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Patent
US06750341B2

Procedure details

Isopropanol (20 mL), 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (Compound II)(“the chlorine derivative”)(2.63 g, 10 mmoles, 1 eq.), 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (Compound I)(“the piperidine derivative”) (2.17 g, 10 mmoles, 1 eq.), sodium carbonate (3.18 g, 30 mmoles, 3 eq.), and potassium iodide (66 mg) were added to a 100 mL round bottom flask and stirred with a magnetic stir bar. The flask was placed in an oil bath at 80° C. and allowed to reflux for 9 hours. The flask was then cooled in an ice bath and the contents was filtered. The filter cake was washed in the filter with a small amount of isopropanol. The filter cake was then slurried 3 times in 20 mL of water and filtered. The resulting slurry was dried to give 3 g of material in 73% yield. The slurry was recrystallized by dissolving in 37 mL of boiling isopropanol, filtered hot and allowed to cool and filtered to give material which had a purity of 99.7% and an overall yield of 60%.
Quantity
2.17 g
Type
reactant
Reaction Step One
Quantity
3.18 g
Type
reactant
Reaction Step One
Quantity
66 mg
Type
catalyst
Reaction Step One
Quantity
20 mL
Type
solvent
Reaction Step One
Yield
73%

Identifiers

REACTION_CXSMILES
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C:7]2=[N:6][C:5]=1[CH3:15].[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[K+].C(O)(C)C>[CH3:15][C:5]1[N:6]=[C:7]2[N:8]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:10])[C:4]=1[CH2:3][CH2:2][N:27]1[CH2:26][CH2:25][CH:24]([C:21]2[C:20]3[CH:30]=[CH:31][C:17]([F:16])=[CH:18][C:19]=3[O:23][N:22]=2)[CH2:29][CH2:28]1 |f:2.3.4,5.6|

Inputs

Step One
Name
Quantity
2.63 g
Type
reactant
Smiles
ClCCC1=C(N=C2N(C1=O)CCCC2)C
Name
Quantity
2.17 g
Type
reactant
Smiles
FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1
Name
Quantity
3.18 g
Type
reactant
Smiles
C([O-])([O-])=O.[Na+].[Na+]
Name
Quantity
66 mg
Type
catalyst
Smiles
[I-].[K+]
Name
Quantity
20 mL
Type
solvent
Smiles
C(C)(C)O

Conditions

Stirring
Type
CUSTOM
Details
stirred with a magnetic stir bar
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
The flask was placed in an oil bath at 80° C.
TEMPERATURE
Type
TEMPERATURE
Details
to reflux for 9 hours
Duration
9 h
TEMPERATURE
Type
TEMPERATURE
Details
The flask was then cooled in an ice bath
FILTRATION
Type
FILTRATION
Details
the contents was filtered
WASH
Type
WASH
Details
The filter cake was washed in the
FILTRATION
Type
FILTRATION
Details
filter with a small amount of isopropanol
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The resulting slurry was dried

Outcomes

Product
Name
Type
product
Smiles
CC1=C(C(=O)N2CCCCC2=N1)CCN3CCC(CC3)C=4C=5C=CC(=CC5ON4)F
Measurements
Type Value Analysis
AMOUNT: MASS 3 g
YIELD: PERCENTYIELD 73%
YIELD: CALCULATEDPERCENTYIELD 73.1%

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
US06750341B2

Procedure details

Isopropanol (20 mL), 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (Compound II)(“the chlorine derivative”)(2.63 g, 10 mmoles, 1 eq.), 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (Compound I)(“the piperidine derivative”) (2.17 g, 10 mmoles, 1 eq.), sodium carbonate (3.18 g, 30 mmoles, 3 eq.), and potassium iodide (66 mg) were added to a 100 mL round bottom flask and stirred with a magnetic stir bar. The flask was placed in an oil bath at 80° C. and allowed to reflux for 9 hours. The flask was then cooled in an ice bath and the contents was filtered. The filter cake was washed in the filter with a small amount of isopropanol. The filter cake was then slurried 3 times in 20 mL of water and filtered. The resulting slurry was dried to give 3 g of material in 73% yield. The slurry was recrystallized by dissolving in 37 mL of boiling isopropanol, filtered hot and allowed to cool and filtered to give material which had a purity of 99.7% and an overall yield of 60%.
Quantity
2.17 g
Type
reactant
Reaction Step One
Quantity
3.18 g
Type
reactant
Reaction Step One
Quantity
66 mg
Type
catalyst
Reaction Step One
Quantity
20 mL
Type
solvent
Reaction Step One
Yield
73%

Identifiers

REACTION_CXSMILES
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C:7]2=[N:6][C:5]=1[CH3:15].[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[K+].C(O)(C)C>[CH3:15][C:5]1[N:6]=[C:7]2[N:8]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:10])[C:4]=1[CH2:3][CH2:2][N:27]1[CH2:26][CH2:25][CH:24]([C:21]2[C:20]3[CH:30]=[CH:31][C:17]([F:16])=[CH:18][C:19]=3[O:23][N:22]=2)[CH2:29][CH2:28]1 |f:2.3.4,5.6|

Inputs

Step One
Name
Quantity
2.63 g
Type
reactant
Smiles
ClCCC1=C(N=C2N(C1=O)CCCC2)C
Name
Quantity
2.17 g
Type
reactant
Smiles
FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1
Name
Quantity
3.18 g
Type
reactant
Smiles
C([O-])([O-])=O.[Na+].[Na+]
Name
Quantity
66 mg
Type
catalyst
Smiles
[I-].[K+]
Name
Quantity
20 mL
Type
solvent
Smiles
C(C)(C)O

Conditions

Stirring
Type
CUSTOM
Details
stirred with a magnetic stir bar
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
The flask was placed in an oil bath at 80° C.
TEMPERATURE
Type
TEMPERATURE
Details
to reflux for 9 hours
Duration
9 h
TEMPERATURE
Type
TEMPERATURE
Details
The flask was then cooled in an ice bath
FILTRATION
Type
FILTRATION
Details
the contents was filtered
WASH
Type
WASH
Details
The filter cake was washed in the
FILTRATION
Type
FILTRATION
Details
filter with a small amount of isopropanol
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The resulting slurry was dried

Outcomes

Product
Name
Type
product
Smiles
CC1=C(C(=O)N2CCCCC2=N1)CCN3CCC(CC3)C=4C=5C=CC(=CC5ON4)F
Measurements
Type Value Analysis
AMOUNT: MASS 3 g
YIELD: PERCENTYIELD 73%
YIELD: CALCULATEDPERCENTYIELD 73.1%

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
US06750341B2

Procedure details

Isopropanol (20 mL), 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (Compound II)(“the chlorine derivative”)(2.63 g, 10 mmoles, 1 eq.), 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (Compound I)(“the piperidine derivative”) (2.17 g, 10 mmoles, 1 eq.), sodium carbonate (3.18 g, 30 mmoles, 3 eq.), and potassium iodide (66 mg) were added to a 100 mL round bottom flask and stirred with a magnetic stir bar. The flask was placed in an oil bath at 80° C. and allowed to reflux for 9 hours. The flask was then cooled in an ice bath and the contents was filtered. The filter cake was washed in the filter with a small amount of isopropanol. The filter cake was then slurried 3 times in 20 mL of water and filtered. The resulting slurry was dried to give 3 g of material in 73% yield. The slurry was recrystallized by dissolving in 37 mL of boiling isopropanol, filtered hot and allowed to cool and filtered to give material which had a purity of 99.7% and an overall yield of 60%.
Quantity
2.17 g
Type
reactant
Reaction Step One
Quantity
3.18 g
Type
reactant
Reaction Step One
Quantity
66 mg
Type
catalyst
Reaction Step One
Quantity
20 mL
Type
solvent
Reaction Step One
Yield
73%

Identifiers

REACTION_CXSMILES
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C:7]2=[N:6][C:5]=1[CH3:15].[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[K+].C(O)(C)C>[CH3:15][C:5]1[N:6]=[C:7]2[N:8]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:10])[C:4]=1[CH2:3][CH2:2][N:27]1[CH2:26][CH2:25][CH:24]([C:21]2[C:20]3[CH:30]=[CH:31][C:17]([F:16])=[CH:18][C:19]=3[O:23][N:22]=2)[CH2:29][CH2:28]1 |f:2.3.4,5.6|

Inputs

Step One
Name
Quantity
2.63 g
Type
reactant
Smiles
ClCCC1=C(N=C2N(C1=O)CCCC2)C
Name
Quantity
2.17 g
Type
reactant
Smiles
FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1
Name
Quantity
3.18 g
Type
reactant
Smiles
C([O-])([O-])=O.[Na+].[Na+]
Name
Quantity
66 mg
Type
catalyst
Smiles
[I-].[K+]
Name
Quantity
20 mL
Type
solvent
Smiles
C(C)(C)O

Conditions

Stirring
Type
CUSTOM
Details
stirred with a magnetic stir bar
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
The flask was placed in an oil bath at 80° C.
TEMPERATURE
Type
TEMPERATURE
Details
to reflux for 9 hours
Duration
9 h
TEMPERATURE
Type
TEMPERATURE
Details
The flask was then cooled in an ice bath
FILTRATION
Type
FILTRATION
Details
the contents was filtered
WASH
Type
WASH
Details
The filter cake was washed in the
FILTRATION
Type
FILTRATION
Details
filter with a small amount of isopropanol
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The resulting slurry was dried

Outcomes

Product
Name
Type
product
Smiles
CC1=C(C(=O)N2CCCCC2=N1)CCN3CCC(CC3)C=4C=5C=CC(=CC5ON4)F
Measurements
Type Value Analysis
AMOUNT: MASS 3 g
YIELD: PERCENTYIELD 73%
YIELD: CALCULATEDPERCENTYIELD 73.1%

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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