Sodium Iodide → Decloxizine

HRID 1169116Notes

Reaction equation

HRID 1169116 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])[CH2:12][CH2:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 70048Benzhydrylpiperazine

Product 1

HCID 71135Decloxizine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.00 g of 1-(diphenylmethyl)piperazine was dissolved in 10 ml of N,N-dimethylformamide; 0.42 ml of 2-(2-chloroethoxy)ethanol, 0.59 g of sodium iodide and 0.66 g of potassium carbonate were added, followed by stirring at 100° C. for 1 hour. Ice water was added, followed by extraction with ethyl acetate; the extract was washed with saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with dichloromethane:ethyl acetate:methanol (10:10:1). The desired fraction was collected and concentrated to yield 1.47 g of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe extract was washed with saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with dichloromethane:ethyl acetate:methanol (10:10:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-069ec2ff525e4559a2a1096efb4c65fd
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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