Dimethylformamide → HCID 58902472, compound

HRID 1640132Notes

Reaction equation

HRID 1640132 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[OH:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>CCOC(C)=O.O>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[O:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate

Product 1

HCID 58902472HCID 58902472, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Into a 1-neck round-bottom flask was added 4-fluoro-3-nitrobenzotrifluoride (1.62 mL, 0.012 mol), tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate (4.00 g, 0.017 mol), cesium carbonate (11.3 g, 0.035 mol), and DMF (100 mL). The reaction was allowed to stir and heat at 60° C. overnight. The reaction mixture was allowed to cool to rt and diluted with EtOAc and water. The organic solution was separated, washed with water and brine, and concentrated to yellow oil. The residue was purified by column chromatography to give tert-butyl 4-{2-[2-nitro-4-(trifluoromethyl)phenoxy]ethyl}piperazine-1-carboxylate (2.44 g, 48%) as a brown oil. LCMS: (AA) ES+420.1.

Workup

  1. temperatureto cool to rt
  2. customThe organic solution was separated
  3. washwashed with water and brine
  4. concentrationconcentrated to yellow oil
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-790cc9557a124fb1a32461ec17a5ac59
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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