Hydrochloric Acid → Tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate

HRID 2425600Notes

Reaction equation

HRID 2425600 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.Cl.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:19][C:2]([F:1])([F:18])[CH2:3][N:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20294522Tert-butyl 4-(2,2,2-trifluoroacetyl)piperazine-1-carboxylate

Product 1

HCID 16748694Tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(2,2,2-trifluoroacetyl)piperazine-1-carboxylate (0.908 g, 3.22 mmol) was added to a solution of borane-tetrahydrofuran complex (8 mmol) in tetrahydrofuran (24 mL) and the reaction mixture was heated at reflux for 2 h. After cooling, 2 N hydrochloric acid (4 mL) was carefully added and the reaction mixture was stirred until gas evolution ceased and then diluted with ethyl acetate (200 mL). Aqueous sodium hydroxide (0.2 M, 75 mL) was then added and the phases were separated. The organic layer was dried over sodium sulfate and evaporated. The residue was purified by column chromatography (eluting with 20% ethyl acetate in hexanes) to give tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate (0.627 g, 73%) as a white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. customthe phases were separated
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography (eluting with 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c341896ce28b411c9b5e36afc86e7c37
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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