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molecular formula C20H21ClN2 B194729 8-chloro-11-(1-methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine CAS No. 38092-89-6

8-chloro-11-(1-methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Cat. No. B194729
M. Wt: 324.8 g/mol
InChI Key: VLXSCTINYKDTKR-UHFFFAOYSA-N
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Patent
US04863931

Procedure details

Ethyl chloroformate (40.4 mL; 45.9 g; 0.423 mol) was added slowly to a hot (-80° C) toluene solution (320 mL) of the 8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (45.7 g; 0.141 mol) from Example 1E containing the two corresponding fluoro-substituted compounds of the invention. Following complete addition, the temperature was maintained at 80° C. for 1 h. The reaction mixture was cooled to ambient temperature and the toluene solution washed with water which was adjusted to pH 10 with aqueous sodium hydroxide. The organic layer was concentrated to a residue which was dissolved in hot acetonitrile and decolorized with charcoal. The solution was concentrated to a crystalline slurry which was cooled (5° C). 8-chloro-6,11-dihydro-11-(1-ethoxycarbonyl-4-piperidylidene)-5H-benzo[5,6]cyclohepta [1,2-b]pyridine containing the two corresponding fluoro-substituted compounds of the invention as discussed in Examples 1G below was isolated by filtration yielding 42.4 g: m.p. 134.5°-136° C.; NMR (400 MHz, CDCl3)δ1.25 (t,3H,J=8 Hz), 2.3-2.4 (m,3H), 2.4-2.5 (m,1H), 2.7-2.9 (m,2H), 3.1-3.2 (m,2H), 3.3-3.4 (m,2H), 3.81 (br s, 2H), 4.13 (q,2H,J=8 Hz), 7.1-7.3 (m,4H), 7.43 (dd,1H,J=9,2 Hz), 8.40 (d,1H,J=5 Hz); mass spectrum, m/e (relative intensity) 385M+3 (35), 383 M+1 (100). Anal. Calcd. for C22H23N2ClO2 : C,69.00; H,6.05; N,7.32; Cl9.26. Found: C,69.37; H,6.09; N,7.35; Cl 9.37.
Quantity
40.4 mL
Type
reactant
Reaction Step One
Quantity
320 mL
Type
solvent
Reaction Step One
[Compound]
Name
fluoro-substituted
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
( 35 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
[Compound]
Name
( 100 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
[Compound]
Name
Cl
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five

Identifiers

REACTION_CXSMILES
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:21](=[C:22]3[CH2:27][CH2:26][N:25](C)[CH2:24][CH2:23]3)[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH2:14][CH2:13][C:12]=2[CH:29]=1>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:21](=[C:22]3[CH2:23][CH2:24][N:25]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:26][CH2:27]3)[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH2:14][CH2:13][C:12]=2[CH:29]=1

Inputs

Step One
Name
Quantity
40.4 mL
Type
reactant
Smiles
ClC(=O)OCC
Name
Quantity
45.7 g
Type
reactant
Smiles
ClC=1C=CC2=C(CCC=3C(=NC=CC3)C2=C2CCN(CC2)C)C1
Name
Quantity
320 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Step Two
Name
fluoro-substituted
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Three
Name
( 35 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
( 100 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Five
Name
Cl
Quantity
0 (± 1) mol
Type
reactant
Smiles

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
80 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
addition
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was cooled to ambient temperature
WASH
Type
WASH
Details
the toluene solution washed with water which
CONCENTRATION
Type
CONCENTRATION
Details
The organic layer was concentrated to a residue which
DISSOLUTION
Type
DISSOLUTION
Details
was dissolved in hot acetonitrile
CONCENTRATION
Type
CONCENTRATION
Details
The solution was concentrated to a crystalline slurry which
TEMPERATURE
Type
TEMPERATURE
Details
was cooled (5° C)
CUSTOM
Type
CUSTOM
Details
below was isolated by filtration
CUSTOM
Type
CUSTOM
Details
yielding 42.4 g

Outcomes

Product
Name
Type
Smiles
ClC=1C=CC2=C(CCC=3C(=NC=CC3)C2=C2CCN(CC2)C(=O)OCC)C1

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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