Piperazine → Trifluoroacetylpiperazine

HRID 1973024Notes

Reaction equation

HRID 1973024 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C1COCC1>[F:9][C:2]([F:1])([F:8])[C:3]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:5]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 7172020TrifluoroacetylpiperazineYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl trifluoroacetate (34.54 mL, 287.33 mmol) was added to a suspension of piperazine (25.0 g, 287.33 mmol) in THF (250 mL) at room temperature under nitrogen and stirred for 30 min and concentrated to remove solvent. The oily residue was taken up in ether and filtered and the filter cake was washed with ether. The filtrate was concentrated to give a clear oil (24.37 g, 47%). LC-MS [M+H]+=183.1, RT=1.07 min.

Workup

  1. concentrationconcentrated
  2. customto remove solvent
  3. filtrationfiltered
  4. washthe filter cake was washed with ether
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ac579c001e0a42cbbce11956151d1f4c
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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