Sodium Iodide → 1-(3,4-Dimethoxyphenethyl)-4-(2-(4-chlorophenoxy)ethyl)piperazine

HRID 1928543Notes

Reaction equation

HRID 1928543 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CC1C=CC(S(O[CH2:32][CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)(=O)=O)=CC=1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH2:32][CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107349442-(4-Chlorophenoxy)ethyl 4-methylbenzene-1-sulfonateHCID 529835491-(3,4-Dimethoxyphenethyl)piperazine dihydrochloride

Product 1

HCID 247387281-(3,4-Dimethoxyphenethyl)-4-(2-(4-chlorophenoxy)ethyl)piperazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the solution of 1-(3,4-dimethoxyphenethyl)piperazine dihydrochloride (502 mg, 1.55 mmol) and 2-(4-chlorophenoxy)ethyl 4-methylbenzenesulfonate (460 mg, 1.4 mmol) in acetone (20 mL) was added NaI (465 mg, 3.1 mmol) and K2CO3 (1.1 g, 7.0 mmol). The reaction mixture was then refluxed overnight and concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. The resulting residue was purified by column chromatography to afford 1-(3,4-dimethoxyphenethyl)-4-(2-(4-chlorophenoxy)ethyl)piperazine which was suspended in 6 N HCl(aq). (pH=3). The precipitate was filtered, washed with cold ethanol, and dried to afford the title compound (350 mg, 52%).

Workup

  1. temperatureThe reaction mixture was then refluxed overnight
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-9c8e6815c84e4688aca8d2ca44e6bad7
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Reaction notes

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