Barium Carbonate → Loratadine

HRID 2351575Notes

Reaction equation

HRID 2351575 reaction equation
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

Participants

6

Reactant 3

HCID 10563Barium CarbonateHCID 10928Ethyl chloroformateHCID 19846460HCID 19846460, compound

Product 1

HCID 3957Loratadine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

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.

Workup

  1. extractionthe product extracted into ethvl acetate
  2. customThe solvent is removed
  3. custompurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-5fa9f65cb7f344158a3e6c0e2203301d
Source dataset
uspto-grants-1989_10
Patent number
US04873335

Reaction notes

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