Dimethylformamide → HCID 7961565, compound

HRID 2195631Notes

Reaction equation

HRID 2195631 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.CN(C)C=O.F[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=1[N+:24]([O-:26])=[O:25]>O>[N+:24]([C:15]1[CH:16]=[C:17]([C:20]([F:21])([F:22])[F:23])[CH:18]=[CH:19][C:14]=1[N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]1[CH3:1])([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 6427443(S)-(+)-2-Methylpiperidine

Product 1

HCID 7961565HCID 7961565, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-2-methylpiperidine (270 μl, 2.24 mmol, commercially available product) was added at room temperature to an N,N-dimethylformamide (DMF; 0.5 ml) solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (211 mg, 1.00 mmol, commercially available product). The resulting mixture was stirred for two hours. 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 (20 g, hexane/ethyl acetate=12/1). Thus, (S)-1-[2-nitro-4-(trifluoromethyl)phenyl]-2-methylpiperidine (286 mg, 99.2%) was yielded as an orange-colored oily material.

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 (20 g, hexane/ethyl acetate=12/1)

Sources & evidence

ORD record
ord-149933538ca24c789be6749d73caaa93
Source dataset
uspto-grants-2012_12
Patent number
US08338362B2

Reaction notes

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