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molecular formula C12H15ClF2N2O B1148542 (2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride CAS No. 135634-18-3

(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride

Cat. No. B1148542
M. Wt: 276.71
InChI Key:
Attention: For research use only. Not for human or veterinary use.
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Patent
US07307168B2

Procedure details

To a solution of 36.0 g (0.16 mole) of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one in 800 ml of acetonitrile 44.3 g of 4-(2,4-difluoro-benzoyl)-piperidine-oxime-hydrochloride, 33.6 g of sodium hydrogen carbonate and 0.66 g (4 millimoles) of potassium iodide are added. The reaction mixture is refluxed for 5 hours, cooled to room temperature and the solvent is removed in vacuo. The residue is taken up in 700 ml of water and extracted twice with 600 ml of dichloromethane each. The combined organic layers are dried over sodium sulfate and evaporated in vacuo. Thus 63.7 g of the title compound are obtained. Yield 92.5%. M.p.: 180-183° C.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
33.6 g
Type
reactant
Reaction Step One
Quantity
800 mL
Type
solvent
Reaction Step One
Quantity
0.66 g
Type
catalyst
Reaction Step One
Yield
92.5%

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].Cl.[F:17][C:18]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:19]=1[C:20](=[N:27][OH:28])[CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])O.[Na+]>C(#N)C.[I-].[K+]>[F:17][C:18]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:19]=1[C:20](=[N:27][OH:28])[CH:21]1[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][C:4]2[C:9](=[O:10])[N:8]3[CH2:11][CH2:12][CH2:13][CH2:14][C:7]3=[N:6][C:5]=2[CH3:15])[CH2:23][CH2:22]1 |f:1.2,3.4,6.7|

Inputs

Step One
Name
Quantity
36 g
Type
reactant
Smiles
ClCCC1=C(N=C2N(C1=O)CCCC2)C
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl.FC1=C(C(C2CCNCC2)=NO)C=CC(=C1)F
Name
Quantity
33.6 g
Type
reactant
Smiles
C(O)([O-])=O.[Na+]
Name
Quantity
800 mL
Type
solvent
Smiles
C(C)#N
Name
Quantity
0.66 g
Type
catalyst
Smiles
[I-].[K+]

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 refluxed for 5 hours
Duration
5 h
CUSTOM
Type
CUSTOM
Details
the solvent is removed in vacuo
EXTRACTION
Type
EXTRACTION
Details
extracted twice with 600 ml of dichloromethane each
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic layers are dried over sodium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated in vacuo

Outcomes

Product
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 63.7 g
YIELD: PERCENTYIELD 92.5%

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 36.0 g (0.16 mole) of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one in 800 ml of acetonitrile 44.3 g of 4-(2,4-difluoro-benzoyl)-piperidine-oxime-hydrochloride, 33.6 g of sodium hydrogen carbonate and 0.66 g (4 millimoles) of potassium iodide are added. The reaction mixture is refluxed for 5 hours, cooled to room temperature and the solvent is removed in vacuo. The residue is taken up in 700 ml of water and extracted twice with 600 ml of dichloromethane each. The combined organic layers are dried over sodium sulfate and evaporated in vacuo. Thus 63.7 g of the title compound are obtained. Yield 92.5%. M.p.: 180-183° C.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
33.6 g
Type
reactant
Reaction Step One
Quantity
800 mL
Type
solvent
Reaction Step One
Quantity
0.66 g
Type
catalyst
Reaction Step One
Yield
92.5%

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].Cl.[F:17][C:18]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:19]=1[C:20](=[N:27][OH:28])[CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])O.[Na+]>C(#N)C.[I-].[K+]>[F:17][C:18]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:19]=1[C:20](=[N:27][OH:28])[CH:21]1[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][C:4]2[C:9](=[O:10])[N:8]3[CH2:11][CH2:12][CH2:13][CH2:14][C:7]3=[N:6][C:5]=2[CH3:15])[CH2:23][CH2:22]1 |f:1.2,3.4,6.7|

Inputs

Step One
Name
Quantity
36 g
Type
reactant
Smiles
ClCCC1=C(N=C2N(C1=O)CCCC2)C
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl.FC1=C(C(C2CCNCC2)=NO)C=CC(=C1)F
Name
Quantity
33.6 g
Type
reactant
Smiles
C(O)([O-])=O.[Na+]
Name
Quantity
800 mL
Type
solvent
Smiles
C(C)#N
Name
Quantity
0.66 g
Type
catalyst
Smiles
[I-].[K+]

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 refluxed for 5 hours
Duration
5 h
CUSTOM
Type
CUSTOM
Details
the solvent is removed in vacuo
EXTRACTION
Type
EXTRACTION
Details
extracted twice with 600 ml of dichloromethane each
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic layers are dried over sodium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated in vacuo

Outcomes

Product
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 63.7 g
YIELD: PERCENTYIELD 92.5%

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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