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

HRID 1514157

Reaction equation

HRID 1514157 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].Br[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[N+:2]([C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 27602151-(3-nitrophenyl)piperazine Hydrochloride

Product 1

HCID 59536469Ethyl 3-[4-(3-nitrophenyl)piperazino]propanoateYield 91.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(3-nitrophenyl)piperazine hydrochloride (2.6 g, 10.66 mmol), ethyl 3-bromopropionate (2.41 g, 1.7 mL, 13.32 mmol), potassium carbonate (6.1 g, 44.13 mmol) and a catalytic amount of potassium iodide in acetonitrile (30 mL) was heated at reflux for 18 hrs. After cooling to 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 to afford 3.00 g (91.5%) ethyl 3-[4-(3-nitrophenyl)piperazino]propanoate D6 as an orange oil which crystallised on standing.

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

Sources & evidence

ORD record
ord-d881c4344a1544e2addc24a5c274a5da
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Linked notes

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