Potassium Carbonate → 1-[3-(4-Iodophenoxy)propyl]-2-methylpyrrolidine

HRID 548624Notes

Reaction equation

HRID 548624 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.Cl[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[I-].[Na+]>[I:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][CH2:8][N:3]2[CH2:4][CH2:5][CH2:6][CH:2]2[CH3:1])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 158955201-(3-Chloropropoxy)-4-iodobenzene

Product 1

HCID 575502501-[3-(4-Iodophenoxy)propyl]-2-methylpyrrolidineYield 90.4%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

2-methylpyrrolidine a4 (2 g, 23 mmol, 2 eq) is added into a suspension of 1-(3-chloropropoxy)-4-iodobenzene a3 (3.48 g, 11.7 mmol, 1 eq), potassium carbonate (3.24 g, 23 mmol, 2 eq) and sodium iodide (0.035 g, 0.23 mmol, 0.02 eq) in acetonitrile (120 ml), and the mixture is heated at reflux overnight. The solvent is then removed in vacuo, and the residue is dissolved in ethyl acetate. The organic layer is washed twice with a saturated solution of aqueous sodium hydrogenocarbonate, dried over magnesium sulfate, and concentrated in vacuo to give 3.65 g of a yellow oil. This oil is purified by chromatography over silicagel (dichloromethane/methanol/ammonia:98/2/0.2) to afford 2.57 g of 1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine a5 as a yellow oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. customThe solvent is then removed in vacuo
  4. dissolutionthe residue is dissolved in ethyl acetate
  5. washThe organic layer is washed twice with a saturated solution of aqueous sodium hydrogenocarbonate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d22cbdf9f624cd389062ef6de6ea903
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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