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

HRID 655599Notes

Reaction equation

HRID 655599 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 HClaq. (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-34533c4b4589416a81c1fa2ccf42b9ea
Source dataset
uspto-grants-2011_12
Patent number
US08071602B2

Reaction notes

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