Iodoethane → 2-[N-Dodecyl-N-ethylamino]ethanol

HRID 1383936Notes

Reaction equation

HRID 1383936 reaction equation
[CH2:1]([NH:13][CH2:14][CH2:15][OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].I[CH2:18][CH3:19].C(N(CC)C(C)C)(C)C>C(O)(C)C>[CH2:1]([N:13]([CH2:14][CH2:15][OH:16])[CH2:18][CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 855122-(Dodecylamino)ethanol

Product 1

HCID 98815792-[N-Dodecyl-N-ethylamino]ethanolYield 73.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-[Dodecylamino]ethanol (2.0 g, 8.73 mmol), 1-iodoethane (1.63 g, 10.48 mmol) and N,N-diisopropylethylamine (2.51 g,17.5 mmol) in isopropanol (25 ml )were heated under reflux for 4 h. The solvent was then evaporated in vacuo and the residue was diluted with ethyl acetate washed with aqueous sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent followed by chromatography on silica gel (ethyl acetate/methanol 90:10 to 80:20) afforded the title compound (1.65 g, 73%) as a white solid.

Workup

  1. temperatureunder reflux for 4 h
  2. customThe solvent was then evaporated in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with aqueous sodium bicarbonate, brine
  5. dry with materialdried (magnesium sulfate)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-db38d0e3d16c4d3ebc93ca3e4e8acae7
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

Loading…