Water → HCID 57118666, compound

HRID 1856761Notes

Reaction equation

HRID 1856761 reaction equation
[CH:1]1([NH:7][CH2:8][CH:9]([OH:12])[CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:15](Br)[CH3:16].O>O1CCCC1>[CH:1]1([NH:7][CH2:8][CH:9]([O:12][CH2:15][CH3:16])[CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 419885HCID 419885, compound

Product 1

HCID 57118666HCID 57118666, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

N-Cyclohexyl-N-(2-hydroxybutyl)amine (3 g) is dissolved in tetrahydrofuran (50 ml), and thereto is added with stirring sodium hydride (60% oily dispersion, 2.1 g) under ice-cooling, and the mixture is heated with stirring at 60° C. for one hour. To the reaction mixture is added dropwise with stirring ethyl bromide (2.1 g) under ice-cooling, and the mixture is stirred at room temperature for 4 hours. Water is added to the reaction mixture, and the mixture is extracted with ethyl acetate. The extract is concentrated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol:aqueous ammonia=100:10:1) to give N-cyclohexyl-N-(2-ethoxybutyl)amine(1.6 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturethe mixture is heated
  3. temperaturecooling
  4. stirringthe mixture is stirred at room temperature for 4 hours
  5. extractionthe mixture is extracted with ethyl acetate
  6. concentrationThe extract is concentrated under reduced pressure
  7. customto remove the solvent
  8. customthe residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol:aqueous ammonia=100:10:1)

Sources & evidence

ORD record
ord-b0170e957afe4e39a50723f8348894dd
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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