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

HRID 361867Notes

Reaction equation

HRID 361867 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+].O>C(#N)C>[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 4

HCID 962WaterHCID 796132-Chloro-3-nitropyridineHCID 516893Potassium BicarbonateHCID 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 1

HCID 6342AcetonitrileSolvent

Procedure

1-Benzyl-4-[(N-ethylamino)methyl]piperidine (EXAMPLE 261, 5.68 g) and 2-chloro-3-nitropyridine (3.87 g) are dissolved in 96 ml of acetonitrile and 4.05 g of solid potassium bicarbonate is added. The reaction is refluxed for 20 hr, cooled to 20°-25°, poured into water and extracted with ethyl acetate. The organic extracts are dried (sodium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (15% ethyl acetate/hexane to 80% ethyl acetate/hexane) gives the title compound, HRMS calcd. for C20H26N4O2 =354.2056, found=354.2045.

Workup

  1. temperatureThe reaction is refluxed for 20 hr
  2. temperaturecooled to 20°-25°
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts are dried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (15% ethyl acetate/hexane to 80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f6ac66209dc64b27aa6e39f2ac567577
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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