Water → 1-Benzyl-4-[N-ethyl-N-(6-fluoro-3-nitro-2-pyridyl)amino]piperidine

HRID 361859Notes

Reaction equation

HRID 361859 reaction equation
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([F:11])[N:3]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][CH2:26][CH3:27])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]([CH2:26][CH3:27])[C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([F:11])[N:3]=2)[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 106088761-benzyl-N-ethylpiperidin-4-amineHCID 113895462,6-Difluoro-3-nitropyridine

Product 1

HCID 105945621-Benzyl-4-[N-ethyl-N-(6-fluoro-3-nitro-2-pyridyl)amino]piperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

2,6-Difluoro-3-nitropyridine (5.00 g) is dissolved in acetonitrile (10 ml) and 1-benzyl-4-ethylaminopiperidine (EXAMPLE 11, 6.81 g) dissolved in 10 ml of acetonitrile is added via cannula. Then an additional 58 ml of acetonitrile is added and the reaction is cooled to 0°. Then 5.1 g of potassium carbonate is added and the reaction is stirred 10 min and allowed to warm to 20°-25°. After 6 hrs, the reaction is poured into water, extracted with ethyl acetate, washed with saline and dried over sodium sulfate. Flash column chromatography (silica gel; 5% ethyl acetate/hexane to 10% ethyl acetate/hexane) gives the title compound, NMR (300 MHz, CDCl3) 8.22, 7.37-7.23, 6.25, 3.66, 3.55, 3.50, 3.01, 2.10, 1.95, 1.83 and 1.09δ.

Workup

  1. additionis added via cannula
  2. temperaturethe reaction is cooled to 0°
  3. temperatureto warm to 20°-25°
  4. waitAfter 6 hrs
  5. extractionextracted with ethyl acetate
  6. washwashed with saline
  7. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-8e3f8157770946daaa06d6185af0b905
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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