Piperazine → Trifluoroacetylpiperazine

HRID 1157874Notes

Reaction equation

HRID 1157874 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 (CH2Cl2MeOH, 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 (CH2Cl2MeOH, 9:1)

Sources & evidence

ORD record
ord-b5a62841fd0c4cf4a357cb2662b8ef03
Source dataset
uspto-grants-2010_10
Patent number
US07807694B2

Reaction notes

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