4-(10,11-dibromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine → Desloratadine impurity 24

HRID 372159Notes

Reaction equation

HRID 372159 reaction equation
Br[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[C:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[CH:3]1Br>O>[CH:22]1[C:4]2[CH2:3][CH2:2][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[C:6](=[C:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[C:5]=2[CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 203283464-(10,11-dibromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine

Product 1

HCID 1201458Desloratadine impurity 24

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In accordance with the process of the present invention, the starting material, i.e., the 4-(10,11-dibromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine (I) is treated in an inert polar solvent with hydroxide ion, but preferably by dissolving the salt in water, to produce the biologically active 10,11-dihydroxy derivative of 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine (II). The product produced in this manner is biologically active and is a mixture of primarily the cis and trans isomers, the major portion being present in the cis configuration. The cis isomer of the compound may be isolated by selective fractional crystallization.

Sources & evidence

ORD record
ord-7c9e05974cec4258b28a75fbb768f20c
Source dataset
uspto-grants-1978_05
Patent number
US04089864

Reaction notes

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