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molecular formula C23H28F2N4O2 B8742190 Risperidone E-Oxime

Risperidone E-Oxime

Cat. No. B8742190
M. Wt: 430.5 g/mol
InChI Key: BRCINVRBDDVLDW-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US07307168B2

Procedure details

To a suspension of 40 mg (0.9166 millimole) of 55% sodium hydride and 2 ml of tetrahydrofurane 0.1089 g (0.2532 millimole) of 3-[2-[4-[(2,4-difluorophenyl)-(hydroxyimino)-methyl]-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one is added. The reaction mixture is heated to boiling for an hour, whereupon 5 ml of water are added and the mixture is extracted twice with 10 ml of dichloromethane each. The combined organic phases are dried over magnesium sulfate and evaporated in vacuo. Thus 80 mg of the title compound are obtained, yield 77%. According to HPLC analysis the purity of the product is 97.5%.
Quantity
40 mg
Type
reactant
Reaction Step One
Quantity
2 mL
Type
reactant
Reaction Step One
Name
Quantity
5 mL
Type
solvent
Reaction Step Two
Yield
77%

Identifiers

REACTION_CXSMILES
[H-].[Na+].O1CCCC1.F[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16](=[N:37][OH:38])[CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[C:30](=[O:31])[N:29]3[CH2:32][CH2:33][CH2:34][CH2:35][C:28]3=[N:27][C:26]=2[CH3:36])[CH2:19][CH2:18]1>O>[F:15][C:13]1[CH:12]=[CH:11][C:10]2[C:16]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]4[C:30](=[O:31])[N:29]5[CH2:32][CH2:33][CH2:34][CH2:35][C:28]5=[N:27][C:26]=4[CH3:36])[CH2:19][CH2:18]3)=[N:37][O:38][C:9]=2[CH:14]=1 |f:0.1|

Inputs

Step One
Name
Quantity
40 mg
Type
reactant
Smiles
[H-].[Na+]
Name
Quantity
2 mL
Type
reactant
Smiles
O1CCCC1
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
FC1=C(C=CC(=C1)F)C(C1CCN(CC1)CCC1=C(N=C2N(C1=O)CCCC2)C)=NO
Step Two
Name
Quantity
5 mL
Type
solvent
Smiles
O

Conditions

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

Workups

ADDITION
Type
ADDITION
Details
is added
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture is heated
ADDITION
Type
ADDITION
Details
are added
EXTRACTION
Type
EXTRACTION
Details
the mixture is extracted twice with 10 ml of dichloromethane each
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic phases are dried over magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated in vacuo

Outcomes

Product
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
AMOUNT: MASS 80 mg
YIELD: PERCENTYIELD 77%

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
US07307168B2

Procedure details

To a suspension of 40 mg (0.9166 millimole) of 55% sodium hydride and 2 ml of tetrahydrofurane 0.1089 g (0.2532 millimole) of 3-[2-[4-[(2,4-difluorophenyl)-(hydroxyimino)-methyl]-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one is added. The reaction mixture is heated to boiling for an hour, whereupon 5 ml of water are added and the mixture is extracted twice with 10 ml of dichloromethane each. The combined organic phases are dried over magnesium sulfate and evaporated in vacuo. Thus 80 mg of the title compound are obtained, yield 77%. According to HPLC analysis the purity of the product is 97.5%.
Quantity
40 mg
Type
reactant
Reaction Step One
Quantity
2 mL
Type
reactant
Reaction Step One
Name
Quantity
5 mL
Type
solvent
Reaction Step Two
Yield
77%

Identifiers

REACTION_CXSMILES
[H-].[Na+].O1CCCC1.F[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16](=[N:37][OH:38])[CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[C:30](=[O:31])[N:29]3[CH2:32][CH2:33][CH2:34][CH2:35][C:28]3=[N:27][C:26]=2[CH3:36])[CH2:19][CH2:18]1>O>[F:15][C:13]1[CH:12]=[CH:11][C:10]2[C:16]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]4[C:30](=[O:31])[N:29]5[CH2:32][CH2:33][CH2:34][CH2:35][C:28]5=[N:27][C:26]=4[CH3:36])[CH2:19][CH2:18]3)=[N:37][O:38][C:9]=2[CH:14]=1 |f:0.1|

Inputs

Step One
Name
Quantity
40 mg
Type
reactant
Smiles
[H-].[Na+]
Name
Quantity
2 mL
Type
reactant
Smiles
O1CCCC1
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
FC1=C(C=CC(=C1)F)C(C1CCN(CC1)CCC1=C(N=C2N(C1=O)CCCC2)C)=NO
Step Two
Name
Quantity
5 mL
Type
solvent
Smiles
O

Conditions

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

Workups

ADDITION
Type
ADDITION
Details
is added
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture is heated
ADDITION
Type
ADDITION
Details
are added
EXTRACTION
Type
EXTRACTION
Details
the mixture is extracted twice with 10 ml of dichloromethane each
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic phases are dried over magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated in vacuo

Outcomes

Product
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
AMOUNT: MASS 80 mg
YIELD: PERCENTYIELD 77%

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
US07307168B2

Procedure details

To a suspension of 40 mg (0.9166 millimole) of 55% sodium hydride and 2 ml of tetrahydrofurane 0.1089 g (0.2532 millimole) of 3-[2-[4-[(2,4-difluorophenyl)-(hydroxyimino)-methyl]-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one is added. The reaction mixture is heated to boiling for an hour, whereupon 5 ml of water are added and the mixture is extracted twice with 10 ml of dichloromethane each. The combined organic phases are dried over magnesium sulfate and evaporated in vacuo. Thus 80 mg of the title compound are obtained, yield 77%. According to HPLC analysis the purity of the product is 97.5%.
Quantity
40 mg
Type
reactant
Reaction Step One
Quantity
2 mL
Type
reactant
Reaction Step One
Name
Quantity
5 mL
Type
solvent
Reaction Step Two
Yield
77%

Identifiers

REACTION_CXSMILES
[H-].[Na+].O1CCCC1.F[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16](=[N:37][OH:38])[CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[C:30](=[O:31])[N:29]3[CH2:32][CH2:33][CH2:34][CH2:35][C:28]3=[N:27][C:26]=2[CH3:36])[CH2:19][CH2:18]1>O>[F:15][C:13]1[CH:12]=[CH:11][C:10]2[C:16]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]4[C:30](=[O:31])[N:29]5[CH2:32][CH2:33][CH2:34][CH2:35][C:28]5=[N:27][C:26]=4[CH3:36])[CH2:19][CH2:18]3)=[N:37][O:38][C:9]=2[CH:14]=1 |f:0.1|

Inputs

Step One
Name
Quantity
40 mg
Type
reactant
Smiles
[H-].[Na+]
Name
Quantity
2 mL
Type
reactant
Smiles
O1CCCC1
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
FC1=C(C=CC(=C1)F)C(C1CCN(CC1)CCC1=C(N=C2N(C1=O)CCCC2)C)=NO
Step Two
Name
Quantity
5 mL
Type
solvent
Smiles
O

Conditions

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

Workups

ADDITION
Type
ADDITION
Details
is added
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture is heated
ADDITION
Type
ADDITION
Details
are added
EXTRACTION
Type
EXTRACTION
Details
the mixture is extracted twice with 10 ml of dichloromethane each
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic phases are dried over magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated in vacuo

Outcomes

Product
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
AMOUNT: MASS 80 mg
YIELD: PERCENTYIELD 77%

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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