Risperidone-D5
Numéro de catalogue B2424515
Poids moléculaire: 415.524
Clé InChI: RAPZEAPATHNIPO-SGEUAGPISA-N
Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.
Patent
US06803055B2
Procedure details
A mixture of 5.3 parts of 3-(2-chloromethyl)-6,7,8-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride, 4.4 parts of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, 8 parts of sodium carbonate, 0.1 part of potassium iodide, and 90 parts of DMF is stirred overnight at 80°-90° C. After cooling, the reaction mixture is poured into water. The product is filtered off and crystallized from a mixture of DMF and 2-propanol. The product is filtered off and dried, yielding 3.8 parts (46%) of 3-[2-[4(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 170.0° C.
[Compound]
Name
3-(2-chloromethyl)-6,7,8-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[CH3:25][N:26]([CH:28]=[O:29])[CH3:27]>O>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:3][CH2:4][C:5]4[C:28](=[O:29])[N:26]5[CH2:27][CH2:15][CH2:16][CH2:2][C:25]5=[N:7][C:6]=4[CH3:9])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1 |f:1.2.3,4.5|
|
Inputs
Step One
[Compound]
|
Name
|
3-(2-chloromethyl)-6,7,8-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Na+].[Na+]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[I-].[K+]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CN(C)C=O
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
is stirred overnight at 80°-90° C
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
After cooling
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The product is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
crystallized from a mixture of DMF and 2-propanol
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The product is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
Details
Reaction Time |
8 (± 8) h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=C1
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| YIELD: PERCENTYIELD | 46% |
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
US06803055B2
Procedure details
A mixture of 5.3 parts of 3-(2-chloromethyl)-6,7,8-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride, 4.4 parts of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, 8 parts of sodium carbonate, 0.1 part of potassium iodide, and 90 parts of DMF is stirred overnight at 80°-90° C. After cooling, the reaction mixture is poured into water. The product is filtered off and crystallized from a mixture of DMF and 2-propanol. The product is filtered off and dried, yielding 3.8 parts (46%) of 3-[2-[4(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 170.0° C.
[Compound]
Name
3-(2-chloromethyl)-6,7,8-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[CH3:25][N:26]([CH:28]=[O:29])[CH3:27]>O>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:3][CH2:4][C:5]4[C:28](=[O:29])[N:26]5[CH2:27][CH2:15][CH2:16][CH2:2][C:25]5=[N:7][C:6]=4[CH3:9])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1 |f:1.2.3,4.5|
|
Inputs
Step One
[Compound]
|
Name
|
3-(2-chloromethyl)-6,7,8-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Na+].[Na+]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[I-].[K+]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CN(C)C=O
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
is stirred overnight at 80°-90° C
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
After cooling
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The product is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
crystallized from a mixture of DMF and 2-propanol
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The product is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
Details
Reaction Time |
8 (± 8) h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=C1
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| YIELD: PERCENTYIELD | 46% |
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
US06803055B2
Procedure details
A mixture of 5.3 parts of 3-(2-chloromethyl)-6,7,8-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride, 4.4 parts of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, 8 parts of sodium carbonate, 0.1 part of potassium iodide, and 90 parts of DMF is stirred overnight at 80°-90° C. After cooling, the reaction mixture is poured into water. The product is filtered off and crystallized from a mixture of DMF and 2-propanol. The product is filtered off and dried, yielding 3.8 parts (46%) of 3-[2-[4(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 170.0° C.
[Compound]
Name
3-(2-chloromethyl)-6,7,8-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[CH3:25][N:26]([CH:28]=[O:29])[CH3:27]>O>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:3][CH2:4][C:5]4[C:28](=[O:29])[N:26]5[CH2:27][CH2:15][CH2:16][CH2:2][C:25]5=[N:7][C:6]=4[CH3:9])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1 |f:1.2.3,4.5|
|
Inputs
Step One
[Compound]
|
Name
|
3-(2-chloromethyl)-6,7,8-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Na+].[Na+]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[I-].[K+]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CN(C)C=O
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
is stirred overnight at 80°-90° C
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
After cooling
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The product is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
crystallized from a mixture of DMF and 2-propanol
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The product is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
Details
Reaction Time |
8 (± 8) h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=C1
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| YIELD: PERCENTYIELD | 46% |
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. |
