Cyclopentanecarbonyl chloride → 1-Cyclopentanecarbonylpiperazine

HRID 1727175Notes

Reaction equation

HRID 1727175 reaction equation
O.O.O.O.O.O.[NH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH:13]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1>C(O)C>[CH:13]1([C:18]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 78284Cyclopentanecarbonyl chlorideHCID 120181Piperazine, hexahydrate

Product 1

HCID 155127791-Cyclopentanecarbonylpiperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperazine hexahydrate (8.55 g, 44.0 mmol) was dissolved in absolute ethanol (50 ml) and then refluxed for 10 min. Cyclopentanecarbonyl chloride (5.83 g, 44 mmol) was added dropwise at 65° C. and the reaction mixture was refluxed for 30 min and then stirred at room temperature for 18 h. The reaction mixture was cooled, filtered and the filtrate was concentrated in vacuo to give ˜20 ml of solution. The concentrate was cooled and then filtered again. Ethanolic hydrogen chloride was added to the mother liquor, and the reaction mixture was concentrated to give a white solid, which was dissolved in water (15 ml). The solution was basified to pH 14 and the product was extracted with dichloromethane (7×50 ml). The extracts were dried, (Na2SO4) and concentrated to give the title compound as a yellowish residue, which was distilled to give the product (1.28 g, 7.0 mmol, 16%)

Workup

  1. temperaturerefluxed for 10 min
  2. temperaturethe reaction mixture was refluxed for 30 min
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5d00533441384f46bb124744605133f2
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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