Triethylamine → 1-(2,6-Difluoro-4-nitrophenyl)piperidin-4-one

HRID 1512153Notes

Reaction equation

HRID 1512153 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([F:9])[C:7]=1F.O.Cl.[NH:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[F:9][C:6]1[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=[C:2]([F:1])[C:7]=1[N:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723901PiperonylamineHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 218781831-(2,6-Difluoro-4-nitrophenyl)piperidin-4-oneYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 3,4,5-trifluoronitrobenzene (3.894 g, 0.022 mol) and 4-piperidone hydrochloride monohydrate (3.072 g, 0.020 mol) in chloroform (24 ml), was added triethylamine (8.3 ml, 0.06 mol) under stirring. The resulting mixture was heated and stirred at 70° C. for 7 h. After completion of the reaction (TLC), the solvent was evaporated under reduced pressure and the residue diluted with water (10 ml). The separated solid was filtered, washed with water (8 ml) followed by hexane (5 ml) to obtain yellow crystalline solid as a product, 4.8 g, 94% yield M.P.: 130-132° C.; MS: M+1=257 (MH+ 100%) for M.F.: C11H10F2N2O3

Workup

  1. temperatureThe resulting mixture was heated
  2. stirringstirred at 70° C. for 7 h
  3. customAfter completion of the reaction (TLC)
  4. customthe solvent was evaporated under reduced pressure
  5. additionthe residue diluted with water (10 ml)
  6. filtrationThe separated solid was filtered
  7. washwashed with water (8 ml)
  8. customto obtain yellow crystalline solid as a product

Sources & evidence

ORD record
ord-fa38bc2ed7aa4e96a0d24a7e09bb80a9
Source dataset
uspto-grants-2012_07
Patent number
US08217058B2

Reaction notes

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