Welcome to the BenchChem Online Store!
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.
  • Click on QUICK INQUIRY to receive a quote from our team of experts.
  • With the quality product at a COMPETITIVE price, you can focus more on your research.
Patent
US07307168B2

Procedure details

To a solution of 7.0 g (0.0143 mole) of 3-[2-[4-(2,4-difluoro-benzoyl)-piperidino]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 70 ml of pyridine, 5.4 g (0.0777 mole) of hydroxylamine hydrochloride and 100 ml of ethanol 1.6 g (0.0286 mole) of potassium hydroxide are added. The reaction mixture is heated to boiling for 10 hours, cooled to room temperature and the solvent is removed in vacuo. To the residue 100 ml of water are added and the mixture is extracted with 100 ml of dichloromethane. The organic phase is washed twice with 50 ml of water each, dried over anhydrous magnesium sulfate and evaporated. The residual crude product is recrystallized from ethyl acetate. Thus 4.2 g 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 are obtained. Yield 65.1%. According to HPLC analysis the purity of the product is 97.2%.
Quantity
5.4 g
Type
reactant
Reaction Step One
Quantity
100 mL
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
70 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[C:19](=[O:20])[N:18]3[CH2:21][CH2:22][CH2:23][CH2:24][C:17]3=[N:16][C:15]=2[CH3:25])[CH2:8][CH2:7]1)=O.Cl.[NH2:32][OH:33].C(O)C.[OH-].[K+]>N1C=CC=CC=1>[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[C:4](=[N:32][OH:33])[CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[C:19](=[O:20])[N:18]3[CH2:21][CH2:22][CH2:23][CH2:24][C:17]3=[N:16][C:15]=2[CH3:25])[CH2:8][CH2:7]1 |f:1.2,4.5|

Inputs

Step One
Name
Quantity
7 g
Type
reactant
Smiles
FC1=C(C(=O)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=CC(=C1)F
Name
Quantity
5.4 g
Type
reactant
Smiles
Cl.NO
Name
Quantity
100 mL
Type
reactant
Smiles
C(C)O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
70 mL
Type
solvent
Smiles
N1=CC=CC=C1

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture is heated
CUSTOM
Type
CUSTOM
Details
the solvent is removed in vacuo
ADDITION
Type
ADDITION
Details
To the residue 100 ml of water are added
EXTRACTION
Type
EXTRACTION
Details
the mixture is extracted with 100 ml of dichloromethane
WASH
Type
WASH
Details
The organic phase is washed twice with 50 ml of water each,
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over anhydrous magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated
CUSTOM
Type
CUSTOM
Details
The residual crude product is recrystallized from ethyl acetate

Outcomes

Product
Details
Reaction Time
10 h
Measurements
Type Value Analysis
AMOUNT: MASS 4.2 g
YIELD: PERCENTYIELD 65.1%
YIELD: CALCULATEDPERCENTYIELD 68.2%

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 solution of 7.0 g (0.0143 mole) of 3-[2-[4-(2,4-difluoro-benzoyl)-piperidino]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 70 ml of pyridine, 5.4 g (0.0777 mole) of hydroxylamine hydrochloride and 100 ml of ethanol 1.6 g (0.0286 mole) of potassium hydroxide are added. The reaction mixture is heated to boiling for 10 hours, cooled to room temperature and the solvent is removed in vacuo. To the residue 100 ml of water are added and the mixture is extracted with 100 ml of dichloromethane. The organic phase is washed twice with 50 ml of water each, dried over anhydrous magnesium sulfate and evaporated. The residual crude product is recrystallized from ethyl acetate. Thus 4.2 g 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 are obtained. Yield 65.1%. According to HPLC analysis the purity of the product is 97.2%.
Quantity
5.4 g
Type
reactant
Reaction Step One
Quantity
100 mL
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
70 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[C:19](=[O:20])[N:18]3[CH2:21][CH2:22][CH2:23][CH2:24][C:17]3=[N:16][C:15]=2[CH3:25])[CH2:8][CH2:7]1)=O.Cl.[NH2:32][OH:33].C(O)C.[OH-].[K+]>N1C=CC=CC=1>[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[C:4](=[N:32][OH:33])[CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[C:19](=[O:20])[N:18]3[CH2:21][CH2:22][CH2:23][CH2:24][C:17]3=[N:16][C:15]=2[CH3:25])[CH2:8][CH2:7]1 |f:1.2,4.5|

Inputs

Step One
Name
Quantity
7 g
Type
reactant
Smiles
FC1=C(C(=O)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=CC(=C1)F
Name
Quantity
5.4 g
Type
reactant
Smiles
Cl.NO
Name
Quantity
100 mL
Type
reactant
Smiles
C(C)O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
70 mL
Type
solvent
Smiles
N1=CC=CC=C1

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture is heated
CUSTOM
Type
CUSTOM
Details
the solvent is removed in vacuo
ADDITION
Type
ADDITION
Details
To the residue 100 ml of water are added
EXTRACTION
Type
EXTRACTION
Details
the mixture is extracted with 100 ml of dichloromethane
WASH
Type
WASH
Details
The organic phase is washed twice with 50 ml of water each,
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over anhydrous magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated
CUSTOM
Type
CUSTOM
Details
The residual crude product is recrystallized from ethyl acetate

Outcomes

Product
Details
Reaction Time
10 h
Measurements
Type Value Analysis
AMOUNT: MASS 4.2 g
YIELD: PERCENTYIELD 65.1%
YIELD: CALCULATEDPERCENTYIELD 68.2%

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.
© Copyright 2024 BenchChem. All Rights Reserved.