Donepezil
カタログ番号 B133215
分子量: 379.5 g/mol
InChIキー: ADEBPBSSDYVVLD-UHFFFAOYSA-N
注意: 研究専用です。人間または獣医用ではありません。
Patent
US08124783B2
Procedure details
4-[(5,6-Dimethoxy-1-indanon-2-yl)methyl]piperidine (4 g) was taken in acetone (60 ml). To which benzyl chloride (1.92 g), potassium carbonate (2.28 g) and a catalytic quantity of tetrabutylammonium iodide (TBAI) were added. The reaction mixture was heated at 60° C. and reaction was monitored on TLC. Solvent was removed by distillation after reaction completion and the residue was taken in water and extracted with ethyl acetate (100 ml). The organic extract was acidified with cone. HCl. The solvent was evaporated under vacuum to yield the salt as a residue. Yield: 5.14 g.
Quantity
4 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH:7]([CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH2:6]2.[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:22]([N:19]1[CH2:20][CH2:21][CH:16]([CH2:15][CH:7]2[CH2:6][C:5]3[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:8]2=[O:14])[CH2:17][CH2:18]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1 |f:2.3.4,6.7|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
4 g
|
|
Type
|
reactant
|
|
Smiles
|
COC=1C=C2CC(C(C2=CC1OC)=O)CC1CCNCC1
|
Step Two
|
Name
|
|
|
Quantity
|
1.92 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C1=CC=CC=C1)Cl
|
|
Name
|
|
|
Quantity
|
2.28 g
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[K+].[K+]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
catalyst
|
|
Smiles
|
[I-].C(CCC)[N+](CCCC)(CCCC)CCCC
|
Step Three
|
Name
|
|
|
Quantity
|
60 mL
|
|
Type
|
solvent
|
|
Smiles
|
CC(=O)C
|
Step Four
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
60 °C
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
reaction
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Solvent was removed by distillation
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
after reaction completion
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
extracted with ethyl acetate (100 ml)
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
The organic extract
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The solvent was evaporated under vacuum
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to yield the salt as a residue
|
Outcomes
Product
|
Name
|
|
|
Type
|
|
|
Smiles
|
C(C1=CC=CC=C1)N1CCC(CC1)CC1C(C2=CC(=C(C=C2C1)OC)OC)=O
|
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
US08124783B2
Procedure details
4-[(5,6-Dimethoxy-1-indanon-2-yl)methyl]piperidine (4 g) was taken in acetone (60 ml). To which benzyl chloride (1.92 g), potassium carbonate (2.28 g) and a catalytic quantity of tetrabutylammonium iodide (TBAI) were added. The reaction mixture was heated at 60° C. and reaction was monitored on TLC. Solvent was removed by distillation after reaction completion and the residue was taken in water and extracted with ethyl acetate (100 ml). The organic extract was acidified with cone. HCl. The solvent was evaporated under vacuum to yield the salt as a residue. Yield: 5.14 g.
Quantity
4 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH:7]([CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH2:6]2.[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:22]([N:19]1[CH2:20][CH2:21][CH:16]([CH2:15][CH:7]2[CH2:6][C:5]3[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:8]2=[O:14])[CH2:17][CH2:18]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1 |f:2.3.4,6.7|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
4 g
|
|
Type
|
reactant
|
|
Smiles
|
COC=1C=C2CC(C(C2=CC1OC)=O)CC1CCNCC1
|
Step Two
|
Name
|
|
|
Quantity
|
1.92 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C1=CC=CC=C1)Cl
|
|
Name
|
|
|
Quantity
|
2.28 g
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[K+].[K+]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
catalyst
|
|
Smiles
|
[I-].C(CCC)[N+](CCCC)(CCCC)CCCC
|
Step Three
|
Name
|
|
|
Quantity
|
60 mL
|
|
Type
|
solvent
|
|
Smiles
|
CC(=O)C
|
Step Four
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
60 °C
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
reaction
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Solvent was removed by distillation
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
after reaction completion
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
extracted with ethyl acetate (100 ml)
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
The organic extract
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The solvent was evaporated under vacuum
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to yield the salt as a residue
|
Outcomes
Product
|
Name
|
|
|
Type
|
|
|
Smiles
|
C(C1=CC=CC=C1)N1CCC(CC1)CC1C(C2=CC(=C(C=C2C1)OC)OC)=O
|
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. |
