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molecular formula C24H29NO3 B133215 Donepezil CAS No. 142057-79-2

Donepezil

Cat. No. B133215
M. Wt: 379.5 g/mol
InChI Key: ADEBPBSSDYVVLD-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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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
Quantity
1.92 g
Type
reactant
Reaction Step Two
Quantity
2.28 g
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Two
Quantity
60 mL
Type
solvent
Reaction Step Three
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four

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
Quantity
1.92 g
Type
reactant
Reaction Step Two
Quantity
2.28 g
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Two
Quantity
60 mL
Type
solvent
Reaction Step Three
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four

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.
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