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

HRID 361853Notes

Reaction equation

HRID 361853 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(#N)C.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.CCCCCC>[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

7

Reactant 4

HCID 6342AcetonitrileHCID 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 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

2,6-Difluoro-3-nitropyridine (Recl. Trav. Chim., 95, 127-156 (1976) and Tetrahedron Lett., 28, 111-114 (1987), 2.4 g, 15.0 mmol) and 1-benzyl-4-ethylaminopiperidine (EXAMPLE 11, 3.3 g, 15 mmol) are dissolved in 37.5 mmol of acetonitrile at 0°. Then solid potassium carbonate (2.49 g, 18 mmol) is added and the reaction is slowly warmed to 20°-25°. After the reaction is complete by TLC (ethyl acetate/hexane, (25/75)), it is poured into water and extracted with ethyl acetate. The organic phase is washed with saline, dried over sodium sulfate and concentrated under reduced pressure. Purification via flash column chromatography (5% ethyl acetate/hexane to 10% ethyl acetate/hexane) gives the title compound, mp=99°-100°; NMR (300 MHz, CDCl3) 8.00, 7.13-7.04, 6.02, 3.43, 3.31, 3.28, 2.77, 1.85, 1.71, 1.63 and 0.86δ; CMR (75 MHz, CDCl3) 163.5, 160.2, 151.2, 140.9, 130.4, 128.9, 128.0, 126.9, 96.9, 62.6, 59.6, 52.9, 38.7, 29.3 and 14.0δ.

Workup

  1. temperaturethe reaction is slowly warmed to 20°-25°
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saline
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification via flash column chromatography (5% ethyl acetate/hexane to 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-75ef3697c5524f449a027fc352fcf650
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

Loading…