Loratadine → Desloratadine

HRID 2202593Notes

Reaction equation

HRID 2202593 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19](C(OCC)=O)[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:27]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:27]=1

Participants

4

Reactant 2

HCID 3957LoratadineHCID 14798Sodium Hydroxide

Product 1

HCID 124087DesloratadineYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate (383 mg, 1 mmol) in ethanol, a 30% sodium hydroxide aqueous solution was added. The mixture was refluxed overnight. The solvent was distilled off, and the resulting residue was dissolved in water and neutralized with concentrated hydrochloric acid. The extraction with ethyl acetate was performed 3 times, and the combined organic layer was dried over magnesium sulfate. The solvent was distilled off, and thus the title compound (290 mg, 93.3%) was obtained as a yellowish white solid.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. distillationThe solvent was distilled off
  3. dissolutionthe resulting residue was dissolved in water and neutralized with concentrated hydrochloric acid
  4. extractionThe extraction with ethyl acetate
  5. dry with materialthe combined organic layer was dried over magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-3f199adf10cc442f9aa33da697a337df
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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