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molecular formula C13H13N3 B1221332 Varenicline CAS No. 249296-44-4

Varenicline

Cat. No. B1221332
M. Wt: 211.26 g/mol
InChI Key: JQSHBVHOMNKWFT-DTORHVGOSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08039620B2

Procedure details

In a 250 ml 4 neck round bottom flask equipped with mechanical stirrer, Thermo pocket were charged DM water (30 ml) and 5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene Tosylate salt (10 g, having a total purity of 99.42% obtained in example 4). The above suspension was stirred for 30 minutes at 25-30° C. To this was added 25% aqueous ammonia solution (5 ml) to adjust the pH to 9.0-10 at 25-30° C., and MDC (30 ml) was added to this solution. The resulting mixture was stirred for 30 minutes at 20-25° C. The organic layer was separated, and the aqueous layer was extracted with MDC (4×30 ml). The combined organic layer was washed with DM water (30 ml). The organic layer was treated with activated carbon (1.0 g), and stirred for 30 minutes at 25-30° C. The resulting solution filtered through celite. Concentration afforded a solid product, i.e. 5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene. (Yield-5 g (95.06% (relative to VRN-Tosylate)), HPLC purity-99.43%).
[Compound]
Name
4
Quantity
250 mL
Type
reactant
Reaction Step One
Quantity
5 mL
Type
reactant
Reaction Step Two
Name
5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene Tosylate salt
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Quantity
30 mL
Type
solvent
Reaction Step Three
Name
5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene

Identifiers

REACTION_CXSMILES
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:12]12[CH2:27][CH:23]([CH2:24][NH:25][CH2:26]1)[C:22]1[CH:21]=[C:20]3[C:15]([N:16]=[CH:17][CH:18]=[N:19]3)=[CH:14][C:13]2=1.N>O>[CH:23]12[CH2:27][CH:12]([CH2:26][NH:25][CH2:24]1)[C:13]1[CH:14]=[C:15]3[C:20]([N:19]=[CH:18][CH:17]=[N:16]3)=[CH:21][C:22]2=1 |f:0.1|

Inputs

Step One
Name
4
Quantity
250 mL
Type
reactant
Smiles
Step Two
Name
Quantity
5 mL
Type
reactant
Smiles
N
Step Three
Name
5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene Tosylate salt
Quantity
0 (± 1) mol
Type
reactant
Smiles
S(=O)(=O)(O)C1=CC=C(C)C=C1.C12C=3C=C4N=CC=NC4=CC3C(CNC1)C2
Name
Quantity
30 mL
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
27.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
The above suspension was stirred for 30 minutes at 25-30° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
obtained in example 4)
CUSTOM
Type
CUSTOM
Details
at 25-30° C.
ADDITION
Type
ADDITION
Details
MDC (30 ml) was added to this solution
STIRRING
Type
STIRRING
Details
The resulting mixture was stirred for 30 minutes at 20-25° C
Duration
30 min
CUSTOM
Type
CUSTOM
Details
The organic layer was separated
EXTRACTION
Type
EXTRACTION
Details
the aqueous layer was extracted with MDC (4×30 ml)
WASH
Type
WASH
Details
The combined organic layer was washed with DM water (30 ml)
ADDITION
Type
ADDITION
Details
The organic layer was treated with activated carbon (1.0 g)
STIRRING
Type
STIRRING
Details
stirred for 30 minutes at 25-30° C
Duration
30 min
FILTRATION
Type
FILTRATION
Details
The resulting solution filtered through celite
CONCENTRATION
Type
CONCENTRATION
Details
Concentration

Outcomes

Product
Details
Reaction Time
30 min
Name
5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene
Type
product
Smiles
C12C=3C=C4N=CC=NC4=CC3C(CNC1)C2

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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