Hydrochloric Acid → Desloratadine

HRID 2260107Notes

Reaction equation

HRID 2260107 reaction equation
CCOC([N:6]1[CH2:27][CH2:26][C:9](=[C:10]2[C:20]3[N:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][C:16]3[CH:15]=[C:14]([Cl:25])[CH:13]=[CH:12][C:11]2=3)[CH2:8][CH2:7]1)=O.C[Si](I)(C)C.Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:25][C:14]1[CH:13]=[CH:12][C:11]2[C:10](=[C:9]3[CH2:8][CH2:7][NH:6][CH2:27][CH2:26]3)[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH2:18][CH2:17][C:16]=2[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3957LoratadineHCID 14798Sodium HydroxideHCID 85247Trimethylsilyl iodide

Product 1

HCID 124087DesloratadineYield 77%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 9.1 g (0.238 mol) of loratadine in 120 mL of dry chloroform, was added 7.5 mL of trimethylsilyl iodide. Then, the mixture was heated to 55°-60° C. under an argon atmosphere overnight. 30 mL of 0.5N HCl was added and the mixture was stirred for some time more. After basifying with NaOH, the resulting solution was extracted with chloroform (2-3 times). The organic phase was dried over sodium sulfate and the solvent was removed, to yield 12.89 g of a residue that was purified by crystallization in acetonitrile. 5.69 g of the desired product was obtained (yield: 77%).

Workup

  1. temperatureThen, the mixture was heated to 55°-60° C. under an argon atmosphere overnight
  2. extractionthe resulting solution was extracted with chloroform (2-3 times)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-d3735b7b7fde44e19e6f25fbd2b59e57
Source dataset
uspto-grants-1995_12
Patent number
US05476856

Reaction notes

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