Piperazine → Trifluoroacetylpiperazine

HRID 8932

Reaction equation

HRID 8932 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])C>CO>[F:12][C:11]([F:14])([F:13])[C:10]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:9]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 7172020TrifluoroacetylpiperazineYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of piperazine (1.444 g, 16.8 mmol) in MeOH (10 mL) was added trifluroacetic acid ethyl ester (2.0 mL, 16.8 mmol) and the mixture stirred at room temperature overnight. The reaction was concentrated and purified by column chromatography on silica gel (CH2Cl2/MeOH, 9:1) to afford the desired mono-protected piperazine adduct (1.77 g, 58%) as a pale yellow oil. 1H NMR (CDCl3) δ 1.70 (br s, 1H), 2.90–2.94 (m, 4H), 3.56–3.59 (m, 2H), 3.64–3.67 (m, 2H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography on silica gel (CH2Cl2/MeOH, 9:1)

Sources & evidence

ORD record
ord-214ef05a35294d9a86a8c36032007d91
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Linked notes

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