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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

To a solution of product of Step C above (118 g, 0.487 mole) in 1.2 L of dry tetrahydrofuran is added 395 mL (2.48 mole/liter, 0.585 mole, 1.2 eg.) of N-methyl-piperidyl magnesium chloride over about 15 minutes maintaining the temperature at 45° C.-50° C. by cooling with water as necessary. The reaction is maintained at 40° C. to 50° C. for about another 30 minutes. Completion of the reaction is determined by thin-layer chromatography. The reaction is quenched to pH below 2 with 2N hydrochloric acid and the resulting solution is stirred at about 25° C. for 1 hour. The bulk of the tetrahydrofuran is removed by distillation and the resulting solution is adjusted to pH 3.5 by the addition of aqueous sodium hydroxide. After cooling to 0° to 5° C., the crystalline hydrochloride salt product is filtered off, washed with ice cold water and dried to constant weight at 60° C. Yield: 168.2 g (HALC purity 94%), m.p. 183°-185° C., 89% of theory.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
N-methyl-piperidyl magnesium chloride
Quantity
395 mL
Type
reactant
Reaction Step One
Quantity
1.2 L
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[C:11]([C:16]#N)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[Mg]Cl.[OH2:27]>O1CCCC1>[ClH:1].[CH3:18][N:19]1[CH2:24][CH2:23][CH:22]([C:16]([C:11]2[C:10]([CH2:9][CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:27])[CH2:21][CH2:20]1 |f:4.5|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC=1C=C(C=CC1)CCC=1C(=NC=CC1)C#N
Name
N-methyl-piperidyl magnesium chloride
Quantity
395 mL
Type
reactant
Smiles
CN1C(CCCC1)[Mg]Cl
Name
Quantity
1.2 L
Type
solvent
Smiles
O1CCCC1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
25 °C
Stirring
Type
CUSTOM
Details
the resulting solution is stirred at about 25° C. for 1 hour
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
maintaining the temperature at 45° C.-50° C.
TEMPERATURE
Type
TEMPERATURE
Details
The reaction is maintained at 40° C. to 50° C. for about another 30 minutes
Duration
30 min
CUSTOM
Type
CUSTOM
Details
The reaction is quenched to pH below 2 with 2N hydrochloric acid
CUSTOM
Type
CUSTOM
Details
The bulk of the tetrahydrofuran is removed by distillation
ADDITION
Type
ADDITION
Details
the resulting solution is adjusted to pH 3.5 by the addition of aqueous sodium hydroxide
TEMPERATURE
Type
TEMPERATURE
Details
After cooling to 0° to 5° C.
FILTRATION
Type
FILTRATION
Details
the crystalline hydrochloride salt product is filtered off
WASH
Type
WASH
Details
washed with ice cold water
CUSTOM
Type
CUSTOM
Details
dried to constant weight at 60° C

Outcomes

Product
Details
Reaction Time
1 h
Name
Type
Smiles
Cl.CN1CCC(CC1)C(=O)C1=NC=CC=C1CCC1=CC(=CC=C1)Cl

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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