Sodium Iodide → 1-[2-(2-Fluorophenyl)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride

HRID 1014950Notes

Reaction equation

HRID 1014950 reaction equation
[Cl-:1].[Cl:2][CH2:3][CH2:4][NH+:5]([CH2:15][CH2:16]Cl)[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][NH2:27].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[ClH:2].[ClH:1].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][N:27]1[CH2:16][CH2:15][N:5]([CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 6433572-(2-Fluorophenyl)ethylamineHCID 66985100HCID 66985100, compound

Product 1

HCID 159505321-[2-(2-Fluorophenyl)ethyl]-4-(3-phenylpropyl)piperazine dihydrochlorideYield 17%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of bis(2-chloroethyl)-(3-phenylpropyl)ammonium chloride (0.593 g, 2 mmol) and 2-(2-fluorophenyl)ethanamine (0.278 g, 2 mmol) in dimethylformamide (6 mL) is added anhydrous potassium carbonate (0.829 g, 6 mmol) and sodium iodide (0.599 g, 4 mmol) successively. The reaction mixture is then stirred at 80° C. for 4.5 hours and then cooled to ambient temperature. Water and ethyl acetate are then added to the resultant reaction mixture. The organic layer is separated, washed 3 times with water and once with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue is dissolved in ethanol. To this solution is added 6 N hydrochloric acid drop wise with cooling until pH 3. The resulting solution is maintained at 4° C. overnight. The resultant crystals are collected by filtration and washed with ethanol and ether to give 108 mg of the title compound (17%).

Workup

  1. temperaturecooled to ambient temperature
  2. customreaction mixture
  3. customThe organic layer is separated
  4. washwashed 3 times with water
  5. dry with materialonce with brine, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in ethanol
  8. additionTo this solution is added 6 N hydrochloric acid
  9. temperaturewith cooling until pH 3
  10. temperatureThe resulting solution is maintained at 4° C. overnight
  11. filtrationThe resultant crystals are collected by filtration
  12. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-6619644b0c584ec0859296d666dafdd3
Source dataset
uspto-grants-2011_07
Patent number
US07985751B2

Reaction notes

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