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Dimethylformamide → tert-Butyl4-[5-(trifluoromethyl)pyridin-3-yl]piperazine-1-carboxylate

HRID 1044563
Notes
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Reaction equation

HRID 1044563 reaction equation
[F-].[K+].IC1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[F:23][C:24]([Si](C)(C)C)([F:26])[F:25].C[N:32](C=O)C>CCOC(C)=O.[Cu]I>[C:19]([O:18][C:16]([N:13]1[CH2:12][CH2:11][N:10]([C:6]2[CH:5]=[N:32][CH:9]=[C:8]([C:24]([F:26])([F:25])[F:23])[CH:7]=2)[CH2:15][CH2:14]1)=[O:17])([CH3:20])([CH3:21])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilane2×HCID 68596930Tert-butyl 4-(3-iodophenyl)piperazine-1-carboxylate

Product 1

HCID 59833555tert-Butyl4-[5-(trifluoromethyl)pyridin-3-yl]piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Copper(I) iodide (0.49 g, 2.6 mmol) and potassium fluoride (0.15 g, 2.6 mmol) in a flask were flame-heated under gentle shaking and at high vacuum until a greenish color appeared. A solution of tert-butyl 4-(3-iodophenyl)piperazine-1-carboxylate (0.5 g, 1.0 mmol) and (trifluoromethyl)trimethylsilane (0.37 g, 2.6 mmol) in DMF (5 mL) was added. The brown solution was stirred at room temperature overnight. More (trifluoromethyl)trimethylsilane (0.37 g) was added. The mixture was heated at 50° C. overnight, diluted with EtOAc and washed with saturated ammonium chloride. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried (MgSO4), concentrated and purified by flash chromatography on silica gel (20% to 40% EtOAc/hexanes) to give 120 mg of desired product. MS calculated for C15H20F3N3O2: (M+H) 332; found 332.1.

Workup

  1. stirringThe brown solution was stirred at room temperature overnight
  2. washwashed with saturated ammonium chloride
  3. extractionThe aqueous layer was extracted with EtOAc three times
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (20% to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9e0bb04e25884271af48f1915293575d
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563582B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes