Potassium Carbonate → 2-Nitro-n-[1-(4-pyridyl)piperidin-4-ylmethyl]aniline

HRID 49836Notes

Reaction equation

HRID 49836 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[N:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][NH2:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:24][CH2:23][CH:20]1[CH2:19][CH2:18][N:17]([C:14]2[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=2)[CH2:22][CH2:21]1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamine

Product 1

HCID 121506972-Nitro-n-[1-(4-pyridyl)piperidin-4-ylmethyl]anilineYield 50.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-fluoronitrobenzene (0.13 mL, 1.3 mmol) and 1-(4-pyridyl)piperidine-4-methylamine (242 mg, 1.27 mmol) in DMF (5 mL) was treated with potassium carbonate (175 mg, 1.3 mmol). After 16 h, the mixture was diluted with EtOAc, the organic layer was washed with water (3×), brine, dried with K2CO3, and concentrated. The residue was dissolved in 5% HOAc in MeOH and loaded onto an SCX ion exchange column. Elution with MeOH followed by 2 M NH3 in MeOH yielded 200 mg of the title compound; which was used without further purification.

Workup

  1. washthe organic layer was washed with water (3×), brine
  2. dry with materialdried with K2CO3
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 5% HOAc in MeOH
  5. washElution with MeOH

Sources & evidence

ORD record
ord-c587c2e4610f4cca90261bf987d20170
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Reaction notes

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