Loratadine
Numéro de catalogue B1675096
Poids moléculaire: 382.9 g/mol
Clé InChI: JCCNYMKQOSZNPW-UHFFFAOYSA-N
Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.
Patent
US04873335
Procedure details
A solution of (1-ethoxycarbonyl-4piperidinyl)[3-[2-(3-chlorophenyl)ethyl]-2pyridinyl]methanone hydrochloride (0.5 g, 1.25 mmol) (prepared by reacting the corresponding 1-methyl-H-piperidinyl compound with ethvl chloroformate) in 1.5 mL of trifluoromethane sulfonic acid is stirred at ambient temperature for 24 hours. The reaction is diluted with ice and water, neutralized with barium carbonate, and the product extracted into ethvl acetate. The solvent is removed and following purification of the residue by silica gel chromatography, 8-chloro-6,11-dihydro-11-(1- ethoxycarbonyl-4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine is obtained.
Name
(1-ethoxycarbonyl-4piperidinyl)[3-[2-(3-chlorophenyl)ethyl]-2pyridinyl]methanone hydrochloride
Quantity
0.5 g
Type
reactant
Reaction Step One
[Compound]
Name
1-methyl-H-piperidinyl
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Identifiers
|
REACTION_CXSMILES
|
Cl.[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]([C:15]2[C:20]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)=[CH:19][CH:18]=[CH:17][N:16]=2)=O)[CH2:9][CH2:8]1)=[O:6])[CH3:3].ClC(OCC)=O.C(=O)([O-])[O-].[Ba+2]>FC(F)(F)S(O)(=O)=O.O>[Cl:29][C:25]1[CH:26]=[CH:27][C:28]2[C:13](=[C:10]3[CH2:11][CH2:12][N:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH2:8][CH2:9]3)[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:20]3[CH2:21][CH2:22][C:23]=2[CH:24]=1 |f:0.1,3.4|
|
Inputs
Step One
|
Name
|
(1-ethoxycarbonyl-4piperidinyl)[3-[2-(3-chlorophenyl)ethyl]-2pyridinyl]methanone hydrochloride
|
|
Quantity
|
0.5 g
|
|
Type
|
reactant
|
|
Smiles
|
Cl.C(C)OC(=O)N1CCC(CC1)C(=O)C1=NC=CC=C1CCC1=CC(=CC=C1)Cl
|
Step Two
[Compound]
|
Name
|
1-methyl-H-piperidinyl
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
ClC(=O)OCC
|
Step Four
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Ba+2]
|
Step Five
|
Name
|
|
|
Quantity
|
1.5 mL
|
|
Type
|
solvent
|
|
Smiles
|
FC(S(=O)(=O)O)(F)F
|
Step Six
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
is stirred at ambient temperature for 24 hours
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the product extracted into ethvl acetate
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The solvent is removed
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
purification of the residue by silica gel chromatography
|
Outcomes
Product
Details
Reaction Time |
24 h |
|
Name
|
|
|
Type
|
product
|
|
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. |
