Water → Hydroxypropyl bispalmitamide monoethanolamide

HRID 1107611Notes

Reaction equation

HRID 1107611 reaction equation
[O-2:1].[Mg+2].O.[OH:4][CH2:5][CH2:6][NH:7][CH2:8][CH:9]([OH:15])[CH2:10][NH:11][CH2:12][CH2:13][OH:14].[C:16](Cl)(=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O1CCOCC1>[OH:4][CH2:5][CH2:6][N:7]([C:31](=[O:1])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])[CH2:8][CH:9]([OH:15])[CH2:10][N:11]([C:16](=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:12][CH2:13][OH:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8206Palmitoyl chlorideHCID 30392362-Propanol, 1,3-bis((2-hydroxyethyl)amino)-HCID 6850729Magnesium monoxide

Product 1

HCID 11193108Hydroxypropyl bispalmitamide monoethanolamideYield 76.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Subsequently, into a 500 ml rounded-flask, were introduced 4.0 g of magnesium oxide and 80 g of distilled water. The mixture was stirred, and was added 8.9 g of N,N'-bis(2-hydroxyethyl)-2-hydroxy-1,3-propanediamine prepared above, and then was added 250 ml of 1,4-dioxane. 26.8 g of palmitoyl chloride was gradually added dropwise to the resulting mixture for 1 hour under violent stirring at a room temperature. After stirring for 2 hours, the mixture was filtered, and then the filtrate was mixed with 200 ml of chloroform, and washed twice with 200 ml of distilled water. The organic phase was seperated; on cooling a precipitated, which was collected and recrystallized from acetone, to give 24.3 g of the title compound as white powder, which was identified by IR and NMR. The results are shown in Table 4.

Workup

  1. customprepared above, and
  2. stirringunder violent stirring at a room temperature
  3. stirringAfter stirring for 2 hours
  4. filtrationthe mixture was filtered
  5. additionthe filtrate was mixed with 200 ml of chloroform
  6. washwashed twice with 200 ml of distilled water
  7. customThe organic phase was seperated
  8. temperatureon cooling a precipitated, which
  9. customwas collected
  10. customrecrystallized from acetone

Sources & evidence

ORD record
ord-cf4fc473027f4db890415995122909db
Source dataset
uspto-grants-2000_05
Patent number
US06060612

Reaction notes

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