Dibenzylamine → HCID 68980847, compound

HRID 1821807Notes

Reaction equation

HRID 1821807 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.[CH2:12]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.ClCCl.O>[CH2:20]([N:19]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 7656DibenzylamineHCID 10340Sodium CarbonateHCID 3453632-Chloro-4-methyl-3-nitropyridine

Product 1

HCID 68980847HCID 68980847, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-chloro-4-methyl-3-nitropyridine (1.06 g, 6.14 mmol) in tetrahydrofuran (12 mL) under an atmosphere of nitrogen were added dibenzylamine (2.4 mL, 13 mmol) and sodium carbonate (684 mg, 6.45 mmol). The mixture was warmed to reflux for 48 h and cooled to room temperature. The mixture was diluted with dichloromethane (100 mL) and water (100 mL), and the layers were separated. The aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic extracts were washed with 1 N HCl (100 mL) and brine (100 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by chromatography (silica gel, 10% ethyl acetate/hexanes) to provide 2-(dibenzylamino)-4-methyl-3-nitropyridine (1.53 g, 4.59 mmol, 75%) as a bright yellow oil which solidified upon standing. Rf 0.52 (67:33 hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ2.32 (3H, s), 4.45 (4H, s), 6.70 (1H, d, J=4.9 Hz), 7.16-7.19 (4H, m), 7.21-7.34 (6H, m), 8.16 (1H, d, J=4.9 Hz); ESI MS m/z 334 [C20H19N3O2+H]+.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for 48 h
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with dichloromethane (2×50 mL)
  5. washThe combined organic extracts were washed with 1 N HCl (100 mL) and brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography (silica gel, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0976e21e359749f7ab0a7988e16c585c
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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