4-Fluoro-3-nitrobenzotrifluoride → HCID 67520715, compound

HRID 2115890Notes

Reaction equation

HRID 2115890 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].[CH3:15][NH:16][CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:15][N:16]([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])[CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 516892Sodium BicarbonateHCID 5663231-Methyl-4-(methylamino)piperidine

Product 1

HCID 67520715HCID 67520715, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (7.5 g, 36 mmol) in THF (180 mL) was added N,1-dimethylpiperidin-4-amine (5.5 g, 43 mmol) and NaHCO3 (6.0 g, 71 mmol). The mixture was stirred at RT and monitored by LCMS for disappearance of starting material. The reaction was filtered, concentrated, and partitioned between H2O and CH2Cl2. The aqueous layer was extracted several times with CH2Cl2, and the organics combined. The organics were washed with brine, dried with MgSO4, filtered, and concentrated to afford the desired product.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. custompartitioned between H2O and CH2Cl2
  4. extractionThe aqueous layer was extracted several times with CH2Cl2
  5. washThe organics were washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6de3dfacf0e24f1a9dfe5bfe0b5d1406
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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