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

HRID 1008051Notes

Reaction equation

HRID 1008051 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-1543d930af884e7492f8622d32a7cc9c
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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