Potassium Iodide → Decloxizine

HRID 1070761Notes

Reaction equation

HRID 1070761 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:14]2[CH2:19][CH2:18][N:17]([CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])[CH2:16][CH2:15]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 70048Benzhydrylpiperazine

Product 1

HCID 71135Decloxizine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

71.7 g (284 mmol) benzhydrylpiperazine, 45 g (361 mmol) 2-(2-chloroethoxy)-ethanol, 43.2 g (312 mmol) potassium carbonate and 9.4 g (57 mmol) potassium iodide are stirred in 400 ml absolute DMF for 8 hours at 75° C. After cooling, the solution is concentrated under vacuum. The residue is distributed between acetic acid ethyl ester and water. The aqueous phase is extracted twice with acetic acid ethyl ester and the combined organic phases are washed three times with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH (90/10): Yield 104 g.

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution is concentrated under vacuum
  3. extractionThe aqueous phase is extracted twice with acetic acid ethyl ester
  4. washthe combined organic phases are washed three times with saturated sodium chloride solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent is removed under vacuum
  7. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH (90/10)

Sources & evidence

ORD record
ord-9a84a390e5bd4374aea4d1dada7191ff
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Reaction notes

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