2-(Dimethylamino)ethanol → HCID 14150950, compound

HRID 1835065Notes

Reaction equation

HRID 1835065 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O[CH2:22][CH2:23][N:24]([CH3:26])[CH3:25]>>[C:1]([O:20][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 79022-(Dimethylamino)ethanol2×HCID 445639Oleic Acid2×

Product 1

HCID 14150950HCID 14150950, compound

Conditions

Temperature
150 °C

Procedure

(a″-1) was synthesized by a dehydrating esterification reaction between oleic acid and N-hydroxyethyl-N,N-dimethylamine. Specifically, a four-neck flask equipped with a stirrer, a temperature gage and a dewatering pipe was charged with 132 g of N-hydroxyethyl-N,N-dimethylamine and 400 g of oleic acid and the mixture was raised to 150° C. The mixture was heated under stirring at this temperature for 4 hours while distilling generated water. The resulting mixture was raised to 180° C. and continuously heated with stirring for 10 hours while 66 g of 2-dimethylaminoethanol was added dropwise. After that, the reaction mixture was cooled to 120° C., unreacted amine was distilled under reduced pressure and the reaction mixture was subjected to distillation to obtain 350 g of the target N-oleoyloxyethyl-N,N-dimethylamine (a″-1).

Workup

  1. customSpecifically, a four-neck flask equipped with a stirrer
  2. temperatureThe mixture was heated
  3. distillationwhile distilling
  4. temperatureThe resulting mixture was raised to 180° C.
  5. temperaturecontinuously heated
  6. stirringwith stirring for 10 hours while 66 g of 2-dimethylaminoethanol
  7. additionwas added dropwise
  8. temperatureAfter that, the reaction mixture was cooled to 120° C.
  9. distillationunreacted amine was distilled under reduced pressure
  10. distillationthe reaction mixture was subjected to distillation

Sources & evidence

ORD record
ord-8a5b70c6e1fa4bf49dc5a96057ac7266
Source dataset
uspto-grants-2004_08
Patent number
US06770617B2

Reaction notes

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