Water → HCID 23062637, compound

HRID 491834Notes

Reaction equation

HRID 491834 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH:11]=[CH2:12].O>C(#N)C>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:12][CH2:11][C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 15458tert-Butyl acrylate3×HCID 780131-Isopropylpiperazine

Product 1

HCID 23062637HCID 23062637, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Isopropylpiperazine (650 mg) is dissolved in acetonitrile (7 ml) and thereto is added t-butyl acrylate (743 μl) under ice-cooling. The reaction solution is warmed to room temperature and stirred for 4 hours, and thereto is added additional t-butyl acrylate (148 μl), and then the mixture is stirred at room temperature for another 10 hours. Additional t-butyl acrylate (222 μl) is added to the reaction solution, and the mixture is stirred for 6 hours, thereto is poured water and the solution is extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol=20/1 followed by 10/1) to give t-butyl 3-(4-isopropylpiperazin-1-yl)propionate (1.18 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for another 10 hours
  3. stirringthe mixture is stirred for 6 hours
  4. extractionthe solution is extracted with ethyl acetate
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure
  9. customThe resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol=20/1 followed by 10/1)

Sources & evidence

ORD record
ord-ec4b5d5ecb7c40b0ac5c82ca10466e33
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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