Dimethylformamide → 1-[2-Nitro-4-(trifluoromethyl)phenyl]piperidine

HRID 2410270Notes

Reaction equation

HRID 2410270 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C=O.Cl[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24]>O>[N+:23]([C:14]1[CH:15]=[C:16]([C:19]([F:20])([F:21])[F:22])[CH:17]=[CH:18][C:13]=1[N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene

Product 1

HCID 27757511-[2-Nitro-4-(trifluoromethyl)phenyl]piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Piperidine (5.50 ml, 55.5 mmol, commercially available product) was added at 0° C. to an N,N-dimethylformamide (DMF; 7 ml) solution of 1-chloro-2-nitro-4-(trifluoromethyl)benzene (5.00 g, 22.4 mmol, commercially available product). The resulting mixture was stirred for 40 minutes. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (200 g, hexane/ethyl acetate=8/1). Thus, 1-[2-nitro-4-(trifluoromethyl)phenyl]piperidine (6.13 g, quant.) was yielded as an orange-colored solid.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (200 g, hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-5135d372cf1b417eaff8824c7b3d02f3
Source dataset
uspto-grants-2014_08
Patent number
US08816089B2

Reaction notes

Loading…