Potassium Iodide → Ethyl 3-[4-(2-methoxyphenyl)piperazino]propanoate

HRID 1514152Notes

Reaction equation

HRID 1514152 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Br[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochloride

Product 1

HCID 12234156Ethyl 3-[4-(2-methoxyphenyl)piperazino]propanoateYield 71.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-methoxyphenyl)piperazine hydrochloride (9.10 g, 39.78 mmol), ethyl 3-bromopropionate (7.29 g, 5.14 mL, 40.29 mmol), potassium carbonate (20.00 g, 144.70 mmol) and a catalytic amount of potassium iodide in acetonitrile (80 mL) was heated at reflux for 18 hrs. After cooling at room temperature the solvent was evaporated under reduced pressure and the residue was taken up in dichloromethane. The organic phase was washed with water, dried over MgSO4 and evaporated to dryness. The resulting orange oil was purified by flash chromatography (Silica gel 60 Å, 45 μm, 50% ethyl acetate in hexane) and afforded 8.30 g (71%) ethyl 3-[4-(2-methoxyphenyl)piperazino]propanoate D1 as an oil.

Workup

  1. temperatureat reflux for 18 hrs
  2. customwas evaporated under reduced pressure
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting orange oil was purified by flash chromatography (Silica gel 60 Å, 45 μm, 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a7b7cc57764947beb1bd628dfede1751
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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