Methyl Palmitate → N-(2,3-dihydroxypropyl)-N-octadecylhexadecanamide

HRID 2260088

Reaction equation

HRID 2260088 reaction equation
[OH:1][CH:2]([CH2:23][OH:24])[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[OH-].[K+].[C:27](OC)(=[O:43])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>>[OH:1][CH:2]([CH2:23][OH:24])[CH2:3][N:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:27](=[O:43])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

4

Reactant 3

HCID 8181Methyl PalmitateHCID 14797Potassium HydroxideHCID 1200883-(Octadecylamino)propane-1,2-diol

Product 1

HCID 15825480N-(2,3-dihydroxypropyl)-N-octadecylhexadecanamide

Procedure

N-(2,3-dihydroxypropyl)-octadecylamine (1.0 g, 0.0029 mole) and potassium hydroxide (0.01 g, 0.18 mmole) were heated to 85° C. under vacuum. Methyl palmitate (0.7885 g, 0.0029 mole) was heated and added dropwise to the reaction. The reaction was heated under vacuum for 6 hours. A waxy off-white solid was obtained (crude yield=1.59 g). The waxy solid was recrystalized from hot hexane (yield=0.99 g).

Workup

  1. additionadded dropwise to the reaction
  2. temperatureThe reaction was heated under vacuum for 6 hours
  3. customA waxy off-white solid was obtained (crude yield=1.59 g)
  4. customThe waxy solid was recrystalized from hot hexane (yield=0.99 g)

Sources & evidence

ORD record
ord-6e22494242a649348c6adabd220c06ea
Source dataset
uspto-grants-1995_12
Patent number
US05476671

Linked notes

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