Potassium Carbonate → 1-Benzyl-4-[N-ethyl-N-(3-nitro-2-pyridinyl)amino]methylpiperidine

HRID 361841Notes

Reaction equation

HRID 361841 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][CH2:16][CH3:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:16][CH3:17])[C:19]2[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 54124174N-((1-Benzylpiperidin-4-yl)methyl)ethanamine

Product 1

HCID 573076871-Benzyl-4-[N-ethyl-N-(3-nitro-2-pyridinyl)amino]methylpiperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1-Benzyl-4-[N-ethylamino]methylpiperidine (EXAMPLE 175, 7.59, 32.64 mmol), 2-chloro-3-nitropyridine (5.17 g, 32.64 mmol) and potassium carbonate (5.41 g, 39.17 mmol) in acetonitrile (0.25M) are refluxed 48 hr. The mixture is diluted with water and extracted with ethyl acetate and then dichloromethane. The combined extracts are dried over sodium sulfate, concentrated and chromatographed (silica gel column, 300 g; eluting with 15-80% ethyl acetate/hexane), to give the title compound, NMR (300 MHz, CD3OD) 8.43, 8.20, 7.42, 6.90, 3.61, 3.52, 3.49, 3.00, 2.10, 1.80, 1.37 and 1.25δ.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts are dried over sodium sulfate
  3. concentrationconcentrated
  4. customchromatographed
  5. wash(silica gel column, 300 g; eluting with 15-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2fe4fd7e5ce34e44b70044a735d5c17a
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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