Triethylamine → (2-Chloro-6-methyl-3-nitropyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amine

HRID 1245942Notes

Reaction equation

HRID 1245942 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13](Cl)[CH:12]=[C:11]([CH3:19])[N:10]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][NH2:32])[CH:21]=1>CN(C=O)C>[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][CH2:26][C:22]2[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=2)[CH:12]=[C:11]([CH3:19])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27848192,4-Dichloro-6-methyl-3-nitropyridineHCID 219130212-(3-Pyridin-3-ylpropoxy)ethanamine

Product 1

HCID 21913307(2-Chloro-6-methyl-3-nitropyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amineYield 38.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (6.1 mL, 44 mmol) was added to a solution of 2,4-dichloro-6-methyl-3-nitropyridine (7.50 g, 36.2 mmol), prepared as described in Part A of Example 1, in anhydrous DMF (160 mL). Neat 2-[3-(pyridin-3-yl)propoxy]ethylamine (6.60 g, 36.6 mmol) was then added, and the mixture was stirred at room temperature for 1.5 hours. The volatiles were then removed under reduced pressure, and the residue was dissolved in chloroform. The solution was washed with 2% aqueous potassium bicarbonate (1×), water (1×), and brine (1×), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide an oil. The crude product was purified by column chromatography on silica gel (600 g, eluting with methanol:ethyl acetate in various ratios) to afford an oil which was dried under reduced pressure to yield 4.9 g of (2-chloro-6-methyl-3-nitropyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amine.

Workup

  1. customprepared
  2. customThe volatiles were then removed under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe solution was washed with 2% aqueous potassium bicarbonate (1×), water (1×), and brine (1×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto provide an oil
  9. customThe crude product was purified by column chromatography on silica gel (600 g, eluting with methanol:ethyl acetate in various ratios)
  10. customto afford an oil which
  11. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-fe5054b02c2d4744b8b8072244b4c977
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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