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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
US04863931

Procedure details

To a solution of [3-[2-(3-chlorophenyl)ethyl]-2-pyridinyl]-1-methyl-4-piperidinyl methanone hydrochloride (59.0 g; 0.15 mol) in 120 mL (120 g; 6.0 mol) of hydrofluoric acid at -35° C. was added boron trifluoride (44.3 g; 0.66 mol) over 1 h. The reaction was quenched using ice water and potassium hydroxide to a final pH of 10. The product was extracted into toluene which was washed with water and brine. The toluene solution was concentrated to a residue which was triturated with hot hexanes. Insoluble salts were removed by filtration and the filtrate was concentrated to give as a main product 45.7 g (HPLC purity 96%, yield 91%) of 8-chloro-6,11-dihydro- 11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine as an off-white solid: mp 116°-119° C.; NMR (200 MHz, CDCl3)δ2.0-2.2 (m,2H), 2.27 (s,3H), 2.3-2.6 (m,4H), 2.6-3.0 (m,4H), 3.3-3.6 (m,2H), 7.0-7.2 (m,4H), 7.44 (dd,1H,J=8, 2 Hz), 8.42 (dd,1H,J=3, 2 Hz); mass spectrum, m/e (rel intensity) 327M+3 (28), 325M+1 (100) Anal. Calcd. for C20H21N2Cl: C,73.94; H,6.52; N,8.63; Cl,10.92. Found: C,73.88; H,6.48; N,8.69; Cl10.80. This material was found to include the two corresponding fluoro-substituted compound of the invention as discussed further below.
Quantity
120 mL
Type
reactant
Reaction Step One
Quantity
44.3 g
Type
reactant
Reaction Step One

Identifiers

REACTION_CXSMILES
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[C:12]([C:17]([CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=O)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1.F.B(F)(F)F>>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[C:17](=[C:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH2:10][CH2:9][C:5]=2[CH:4]=1 |f:0.1|

Inputs

Step One
Name
Quantity
59 g
Type
reactant
Smiles
Cl.ClC=1C=C(C=CC1)CCC=1C(=NC=CC1)C(=O)C1CCN(CC1)C
Name
Quantity
120 mL
Type
reactant
Smiles
F
Name
Quantity
44.3 g
Type
reactant
Smiles
B(F)(F)F

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
The reaction was quenched
EXTRACTION
Type
EXTRACTION
Details
The product was extracted into toluene which
WASH
Type
WASH
Details
was washed with water and brine
CONCENTRATION
Type
CONCENTRATION
Details
The toluene solution was concentrated to a residue which
CUSTOM
Type
CUSTOM
Details
was triturated with hot hexanes
CUSTOM
Type
CUSTOM
Details
Insoluble salts were removed by filtration
CONCENTRATION
Type
CONCENTRATION
Details
the filtrate was concentrated

Outcomes

Product
Name
Type
product
Smiles
ClC=1C=CC2=C(CCC=3C(=NC=CC3)C2=C2CCN(CC2)C)C1
Measurements
Type Value Analysis
AMOUNT: MASS 45.7 g
YIELD: PERCENTYIELD 91%
YIELD: CALCULATEDPERCENTYIELD 93.8%

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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