Sodium Iodide → HCID 66985012, compound

HRID 1014947Notes

Reaction equation

HRID 1014947 reaction equation
[Cl-].Cl[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.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl.[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][NH2:43])=[CH:37][C:36]=1[O:44][CH3:45])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O.C(OCC)(=O)C.O>[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][N:43]2[CH2:16][CH2:15][N:5]([CH2:6][CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:4][CH2:3]2)=[CH:37][C:36]=1[O:44][CH3:45])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 200381Benzeneethanamine, 3-methoxy-4-(phenylmethoxy)-, hydrochlorideHCID 66985100HCID 66985100, compound

Product 1

HCID 66985012HCID 66985012, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of bis(2-chloroethyl)-(3-phenylpropyl)ammonium chloride (116 mg, 0.39 mmol), potassium carbonate (119 mg, 0.86 mmol), sodium iodide (134.9 mg, 0.9 mmol), and 2-(4-(benzyloxy)-3-methoxyphenyl)ethanamine hydrochloride (100 mg, 0.34 mmol) in dimethylformamide (3 ml) is stirred at 70° C. for 5 h and then cooled to ambient temperature. To the resultant mixture is added water and ethyl acetate. The organic layer is washed with brine, dried over anhydrous sodium sulfate, and concentrated. The resulting residue is then purified by column chromatography, eluting with methanol-dichloromethane (1:9) to yield 112 mg of 1-(4-(benzyloxy)-3-methoxyphenethyl)-4-(3-phenylpropyl)piperazine (83%).

Workup

  1. temperaturecooled to ambient temperature
  2. washThe organic layer is washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue is then purified by column chromatography
  6. washeluting with methanol-dichloromethane (1:9)

Sources & evidence

ORD record
ord-d866735a7ae54386843a354525d4280a
Source dataset
uspto-grants-2011_07
Patent number
US07985751B2

Reaction notes

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