Risperidone E-Oxime
Katalognummer B8742190
Molekulargewicht: 430.5 g/mol
InChI-Schlüssel: BRCINVRBDDVLDW-UHFFFAOYSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
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
7 g
Type
reactant
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 |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
FC1=C(C=CC(=C1)F)C(C1CCN(CC1)CCC1=C(N=C2N(C1=O)CCCC2)C)=NO
|
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
7 g
Type
reactant
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 |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
FC1=C(C=CC(=C1)F)C(C1CCN(CC1)CCC1=C(N=C2N(C1=O)CCCC2)C)=NO
|
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. |
