Dimethylformamide → 1-(4-Chloro-2-nitrophenyl)piperidine

HRID 2410294

Reaction equation

HRID 2410294 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]([Cl:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21]>O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 69772,5-DichloronitrobenzeneHCID 8082Piperidine

Product 1

HCID 2853181-(4-Chloro-2-nitrophenyl)piperidineYield 96.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Piperidine (660 μl, 6.66 mmol, commercially available product) was added at room temperature to an N,N-dimethylformamide (DMF; 1 ml) solution of 1,4-dichloro-2-nitrobenzene (390 mg, 2.03 mmol, commercially available product). The resulting mixture was stirred for 18.5 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 (30 g, hexane/ethyl acetate=10/1). Thus, 1-(4-chloro-2-nitrophenyl)piperidine (471 mg, 96.4%) 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 (30 g, hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-ee91ea45b0904751abc05dcff34d888c
Source dataset
uspto-grants-2014_08
Patent number
US08816089B2

Linked notes

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