Piperazine → HCID 66754327, compound

HRID 2167182Notes

Reaction equation

HRID 2167182 reaction equation
FC1C(O[C:9]([CH:11]2[CH2:15][C:14](=[O:16])[NH:13][CH2:12]2)=[O:10])=C(F)C(F)=C(F)C=1F.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(Cl)Cl>C1COCC1>[N:21]1([C:9]([CH:11]2[CH2:12][NH:13][C:14](=[O:16])[CH2:15]2)=[O:10])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 6344DichloromethaneHCID 866401555-Oxo-pyrrolidine-3-carboxylic acid pentafluorophenyl ester

Product 1

HCID 66754327HCID 66754327, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-oxo-pyrrolidine-3-carboxylic acid pentafluorophenyl ester 17 (40.1 mg, 0.0578 mmol) in 2 mL THF extra dry was added piperazine (19.9 mg, 0.231 mmol) at room temperature. The reaction mixture was stirred for 10 hours at room temperature. Afterwards, 20 mL methylene chloride were added. The resulting organic layer was washed with 20 mL of a saturated aqueous solution of sodium hydrogenocarbonate, dried over magnesium sulfate and the solvent was removed in vacuo. Finally, the crude product was purified by chromatography on silica gel (ethyl acetate:methanol 9:1→1:1) to afford the desired 4-(piperazine-1-carbonyl)-pyrrolidin-2-one 18 as a white solid (12.2 mg, 45.91%).

Workup

  1. customdry
  2. washThe resulting organic layer was washed with 20 mL of a saturated aqueous solution of sodium hydrogenocarbonate
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customFinally, the crude product was purified by chromatography on silica gel (ethyl acetate:methanol 9:1→1:1)

Sources & evidence

ORD record
ord-f0bd907618e4449094423690572dd5ca
Source dataset
uspto-grants-2015_06
Patent number
US09045414B2

Reaction notes

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