Piperidine → 53013-41-5

HRID 646873Notes

Reaction equation

HRID 646873 reaction equation
F[C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CCO>[N:12]1([C:2]2[CH:7]=[C:6]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 404969453013-41-5Yield 16.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-difluoronitrobenzene (2.09 g, 13.1 mmol) in EtOH (10 mL) at ambient temperature was added piperidine (3.35 g, 39.4 mmol) dropwise. The reaction was allowed to stir overnight and concentrated in vacuo. The residue was dissolved in EtOAc (100 mL), washed with water (2×100 mL), dried (Na2SO4) and concentrated in vacuo. Purification by silica gel column chromatography (10% EtOAc-hexane) afforded 610 mg (16%) of 2,4-dipiperidinylnitrobenzene as an oil. 2,4-dipiperidinylnitrobenzene (273 mg, 0.94 mmol) was then stirred in the presence of 168 mg of 5% Pd—C in 10 mL of MeOH under H2 for 2 h. The reaction was filtered through Celite and concentrated in vacuo to afford 230 mg of 2,4-dipiperidinylaminobenzene (94%) as an oil. Using a procedure similar to Example 4, step (c), 2,4-dipiperidinylaminobenzene (100 mg, 0.38 mmol) was allowed to react with 5-cyano-furan-2-carbonyl chloride (73 mg, 0.46 mmol) in the presence of DIEA (145 μL, 0.83 mmol) to afford 90 mg 62%) of the title compound as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C22H26N4O2, 379.2 (M+H), found 379.2.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (100 mL)
  3. washwashed with water (2×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatography (10% EtOAc-hexane)

Sources & evidence

ORD record
ord-57b51afd98424800aa7a61f402bf18b4
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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