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Piperazine → 1-[4-(Propan-2-yl)piperazin-1-yl]ethan-1-one

HRID 1003320
Notes
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Reaction equation

HRID 1003320 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[I-].[Na+].[C:9](=[O:12])([O-])[O-].[K+].[K+].Br[CH:16]([CH3:18])[CH3:17].[CH:19](Cl)(Cl)Cl>CO>[C:9]([N:1]1[CH2:6][CH2:5][N:4]([CH:16]([CH3:18])[CH3:17])[CH2:3][CH2:2]1)(=[O:12])[CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 4837PiperazineHCID 5238Sodium IodideHCID 6212ChloroformHCID 63582-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 187964191-[4-(Propan-2-yl)piperazin-1-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Conditions

Temperature
60 °C

Procedure

To 12.95 g of piperazine, 0.75 g of sodium iodide and 3.46 g of potassium carbonate were added successively 25 ml of methanol and 6.15 g of 2-bromopropane and the mixture was stirred at 60° C. for 4 hours. After the addition of chloroform and washing with a saturated aqueous solution of sodium chloride, the mixture was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, 12 ml of acetic anhydride was slowly added and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was poured into ice and chloroform was added and the mixture was neutralized with sodium carbonate. After extracting with chloroform, the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue thus obtained was chromatographed over a silica gel column. The solvent was distilled off and the residue was allowed to stand overnight. The diacetylpiperazine thus precipitated out was filtered off to afford 7.26 g of the title compound as an oily substance.

Workup

  1. washwashing with a saturated aqueous solution of sodium chloride
  2. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure, 12 ml of acetic anhydride
  4. additionwas slowly added
  5. stirringthe mixture was stirred at room temperature for 2.5 hours
  6. additionThe reaction solution was poured into ice and chloroform
  7. additionwas added
  8. extractionAfter extracting with chloroform
  9. dry with materialthe extract was dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue thus obtained
  12. customwas chromatographed over a silica gel column
  13. distillationThe solvent was distilled off
  14. waitto stand overnight
  15. customThe diacetylpiperazine thus precipitated out
  16. filtrationwas filtered off

Sources & evidence

ORD record
ord-ab004de9e77242eeaf0b66d58115bfd2
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06046201

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes