Potassium Iodide → HCID 19880590, compound

HRID 1885403Notes

Reaction equation

HRID 1885403 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.[N:11]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CC(=O)CC>[CH2:20]([O:19][C:17]([N:11]1[CH2:12][CH2:13][N:14]([CH2:2][CH2:3][CH2:4][C:5]2[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=2)[CH2:15][CH2:16]1)=[O:18])[CH3:21]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 2054403-(3-chloropropyl)pyridine

Product 1

HCID 19880590HCID 19880590, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixed solution of 3-(3-chloropropyl)pyridine 1.92 g, ethyl 1-piperazinecarboxylate 1.6 g, anhydrous potassium carbonate 3.0 g, potassium iodide 1 g, tetra-n-butylammonium bromide 0.1 g and 2-butanone 50 ml was refluxed for 24 hours. To the reaction mixture was added water 50 ml, and the product was extracted with ethyl acetate. The extract was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure to yield 1-ethoxycarbonyl-4-[3-(3-pyridyl)propyl]piperazine. This was dissolved in a mixture of 20% sodium hydroxide 25 ml and ethanol 25 ml and the solution refluxed for 2 days. The reaction mixture was concentrated under reduced pressure and to the residue was added ethyl acetate 100 ml and anhydrous magnessium sulfate. After stirring the resultant mixture, the insoluble matter was filtered off. The filtrate was concentrated under reduced pressure to yield 1.56 g of oily 1-[3-(3-pyridyl)propyl]piperazine.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c08f4ae1cab8475a9c18de22bf7c2416
Source dataset
uspto-grants-1992_09
Patent number
US05144035

Reaction notes

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