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molecular formula C20H24Cl2N2O B012217 (3-(3-Chlorophenethyl)pyridin-2-yl)(1-methylpiperidin-4-yl)methanone hydrochloride CAS No. 107256-31-5

(3-(3-Chlorophenethyl)pyridin-2-yl)(1-methylpiperidin-4-yl)methanone hydrochloride

Cat. No. B012217
M. Wt: 379.3 g/mol
InChI Key: YDOROGMYGIAIPT-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US04659716

Procedure details

A solution of 177 g (0.49 mole) of a product of Step D above in 480 mL (814.1 g, 5.31 mole) of trifluoromethanesulfonic acid at 90°-95° C. for 18 hours under nitrogen. Completeness of the reaction is determined by thin-layer chromatography. The cooled reaction is quenched with ice-water and the pH is adjusted to 6 with barium carbonate. The product is extracted into methylene chloride, which is concentrated under reduced pressure to about 1 liter and washed with water. The product is extracted into 1N hydrochloric acid, which is treated with 30 g of Darco, and filtered through celite. The pH of the filtrate is adjusted to 10 with 50% aqueous sodium hydroxide and the product is extracted into methylene chloride, which is removed under reduced pressure. The residue is dissolved in hot hexane, which is filtered to remove insolubles. The filtrate is concentrated to a residual beige powder. Yield: 126 g (HPLC purity 80%), 65% of theory.
Quantity
177 g
Type
reactant
Reaction Step One
Quantity
480 mL
Type
reactant
Reaction Step One

Identifiers

REACTION_CXSMILES
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]([C:11]2[C:16]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)=O)[CH2:5][CH2:4]1.FC(F)(F)S(O)(=O)=O>>[Cl:25][C:21]1[CH:22]=[CH:23][C:24]2[C:9](=[C:6]3[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:16]3[CH2:17][CH2:18][C:19]=2[CH:20]=1 |f:0.1|

Inputs

Step One
Name
Quantity
177 g
Type
reactant
Smiles
Cl.CN1CCC(CC1)C(=O)C1=NC=CC=C1CCC1=CC(=CC=C1)Cl
Name
Quantity
480 mL
Type
reactant
Smiles
FC(S(=O)(=O)O)(F)F

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
The cooled reaction
CUSTOM
Type
CUSTOM
Details
is quenched with ice-water
EXTRACTION
Type
EXTRACTION
Details
The product is extracted into methylene chloride, which
CONCENTRATION
Type
CONCENTRATION
Details
is concentrated under reduced pressure to about 1 liter
WASH
Type
WASH
Details
washed with water
EXTRACTION
Type
EXTRACTION
Details
The product is extracted into 1N hydrochloric acid, which
ADDITION
Type
ADDITION
Details
is treated with 30 g of Darco
FILTRATION
Type
FILTRATION
Details
filtered through celite
EXTRACTION
Type
EXTRACTION
Details
the product is extracted into methylene chloride, which
CUSTOM
Type
CUSTOM
Details
is removed under reduced pressure
DISSOLUTION
Type
DISSOLUTION
Details
The residue is dissolved in hot hexane
FILTRATION
Type
FILTRATION
Details
which is filtered
CUSTOM
Type
CUSTOM
Details
to remove insolubles
CONCENTRATION
Type
CONCENTRATION
Details
The filtrate is concentrated to a residual beige powder

Outcomes

Product

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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