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molecular formula C22H23ClN2O2 B1675096 Loratadine CAS No. 79794-75-5

Loratadine

Cat. No. B1675096
M. Wt: 382.9 g/mol
InChI Key: JCCNYMKQOSZNPW-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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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
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
1.5 mL
Type
solvent
Reaction Step Five
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Six

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
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.
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