Diethylethanolamine → Diethyl[2-(4-nitrophenoxy)ethyl]amine

HRID 2415272Notes

Reaction equation

HRID 2415272 reaction equation
[H-].[Na+].[CH2:3]([N:5]([CH2:9][CH3:10])[CH2:6][CH2:7][OH:8])[CH3:4].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>O1CCCC1>[CH2:3]([N:5]([CH2:9][CH3:10])[CH2:6][CH2:7][O:8][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[CH3:4]

Participants

5

Reactant 3

HCID 7497DiethylethanolamineHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydride

Product 1

HCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amineYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

Sodium hydride (4.8 g, 50% in oil, 100 mmol) was added to a solution of 2-diethylamino-ethanol (11.7 g, 100 mmol) (Aldrich) in tetrahydrofuran (500 mL) and stirred for 15 minutes and then heated to 40° C. for an additional 15 minutes. The mixture was cooled to −10° C. and a solution of 1-fluoro-4-nitrobenzene (10 g, 70 mmol) in tetrahydrofuran (50 mL) was added dropwise and stirred at room temperature for 2 hours. The solvent was evaporated and the residue was dissolved in dichloromethane and washed twice with a 4:1 water/brine mixture. The dichloromethane was evaporated under vacuo and the residue chromatographed on silica gel using 1:1 hexane/ethyl acetate, ethyl acetate, then 20% methanol in dichloromethane. The product fractions were concentrated in vacuo, dissolved in ether, treated with activated charcoal, filtered through Celite™ and concentrated to give 9 g, (54%) of diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine.

Workup

  1. temperatureThe mixture was cooled to −10° C.
  2. stirringstirred at room temperature for 2 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed twice with a 4:1 water/brine mixture
  6. customThe dichloromethane was evaporated under vacuo
  7. customthe residue chromatographed on silica gel using 1:1 hexane/ethyl acetate, ethyl acetate
  8. concentrationThe product fractions were concentrated in vacuo
  9. dissolutiondissolved in ether
  10. additiontreated with activated charcoal
  11. filtrationfiltered through Celite™
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-a6e6038828e8408cad160062b83f4eae
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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