Piperazine → Trifluoroacetylpiperazine
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationThe reaction was concentrated
- 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
Reaction notes
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