Potassium Iodide → 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-[bis(4-fluorophenyl)methyl]piperazine

HRID 1607891Notes

Reaction equation

HRID 1607891 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11]Cl)=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11][N:31]2[CH2:30][CH2:29][N:28]([CH:27]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=3)[CH2:33][CH2:32]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 107793021-[Bis(4-fluorophenyl)methoxy]-2-chloroethane

Product 1

HCID 51960891-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-[bis(4-fluorophenyl)methyl]piperazine

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture containing 12.7 g of 2-[bis(4-fluorophenyl)methoxy]ethyl chloride, 8.6 g of 1-[bis(4-fluorophenyl)methyl]piperazine, 6.2 g of powdered anhydrous potassium carbonate and 0.5 g of potassium iodide in 90ml of methyl isobutyl ketone is refluxed for 20 hours while stirring. Aftercooling down, the mixture is evaporated under reduced pressure and water and ethyl ether are added to the residue. The ethereal phase is washed with water, dried over anhydrous magnesium sulfate and evaporated. The crude product is purified on a Kieselgel column by using a 2:1 mixture of benzene and chloroform as eluant. The appropriate fractions are combined, evaporated and the residue is recrystallized from ethanol to give the aimed compound, m.p.: 87°-88° C.

Workup

  1. temperatureis refluxed for 20 hours
  2. customthe mixture is evaporated under reduced pressure and water and ethyl ether
  3. additionare added to the residue
  4. washThe ethereal phase is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe crude product is purified on a Kieselgel column
  8. additiona 2:1 mixture of benzene and chloroform as eluant
  9. customevaporated
  10. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-daba2ca34f844701a9eaf88308ab45cc
Source dataset
uspto-grants-1989_09
Patent number
US04868184

Reaction notes

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