Piperazine → Piperazine, 1-(1-oxooctadecyl)-

HRID 327497Notes

Reaction equation

HRID 327497 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7](Cl)(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O1CCCC1>[C:7]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 8212Stearoyl chloride

Product 1

HCID 10020929Piperazine, 1-(1-oxooctadecyl)-Yield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20 g of anhydrous piperazine was dissolved in 1,000 ml of tetrahydrofuran and then 33.6 g of stearoyl chloride was added dropwise thereto under stirring and under cooling with ice. The mixture was stirred under cooling with ice for 1 h and tetrahydrofuran was distilled off under reduced pressure. A saturated aqueous solution of sodium hydrogencarbonate was added to the residue. After extraction with 200 ml of chloroform three times, the extract was washed with a saturated aqueous solution of common salt and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=9/1) to obtain 5.1 g of the intended product.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was stirred
  3. temperatureunder cooling with ice for 1 h
  4. distillationtetrahydrofuran was distilled off under reduced pressure
  5. additionA saturated aqueous solution of sodium hydrogencarbonate was added to the residue
  6. extractionAfter extraction with 200 ml of chloroform three times
  7. washthe extract was washed with a saturated aqueous solution of common salt
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-6d3b7ca5295a47daba768e0ab8ba1acf
Source dataset
uspto-grants-1993_12
Patent number
US05273985

Reaction notes

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