2-(Methylamino)ethanol → Dodecyl(2-hydroxyethyl)methylamine

HRID 1700873Notes

Reaction equation

HRID 1700873 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:14][NH:15][CH2:16][CH2:17][OH:18]>C(O)(C)C.CCOCC>[CH3:14][N:15]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:16][CH2:17][OH:18]

Participants

5

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 202821-Iodododecane

Product 1

HCID 10657884Dodecyl(2-hydroxyethyl)methylamineYield 97.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A solution of iodododecane (18.1 g, 61.09 mmol) and 2-(methylamino)ethanol (23.0 g, 0.3 mol) in isopropanol (75 ml) was heated under reflux for 3 h. The cooled mixture was diluted with ether (500 ml), washed with water, brine and dried (magnesium sulfate). Evaporation of the solvent under reduced pressure and distillation of the residue under vacuum gave 14.5 g (97%) of N-methyl-N-dodecylethanolamine as a clear oil: b.p. 100-111° C./0.3 torr (bulb to bulb distillation, air bath temperature).

Workup

  1. temperatureunder reflux for 3 h
  2. washwashed with water, brine
  3. dry with materialdried (magnesium sulfate)
  4. customEvaporation of the solvent
  5. distillationunder reduced pressure and distillation of the residue under vacuum

Sources & evidence

ORD record
ord-46a099bcfddf4b5a8d8f95eada4da5b9
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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