Ethyl 3-aminobenzoate → Ethyl 3-(piperazin-1-yl)benzoate

HRID 1796734Notes

Reaction equation

HRID 1796734 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.Cl[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl>C1(C)C(C)=CC=CC=1>[N:1]1([C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 11400Ethyl 3-aminobenzoateHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 11506913Ethyl 3-(piperazin-1-yl)benzoateYield 70%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ethyl 3-aminobenzoate (1.65 g) was dissolved in xylene (20 ml), and bischloroethylamine hydrochloride (1.79 g) was added to the solution. The mixture was heated under reflux with stirring for two days. The solvent was removed from the reaction solution by distillation under the reduced pressure. Water and a saturated aqueous sodium hydrogencarbonate solution were added to the residue, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=9:1−5:1) to give 1.60 g (70.0%) of ethyl 3-piperazin-1-yl-benzoate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customThe solvent was removed from the reaction solution by distillation under the reduced pressure
  4. additionWater and a saturated aqueous sodium hydrogencarbonate solution were added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was then removed by distillation under the reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=9:1−5:1)

Sources & evidence

ORD record
ord-4256d83bfabd478e8ecadce94d04572d
Source dataset
uspto-grants-2006_04
Patent number
US07030120B2

Reaction notes

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