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

HRID 2260086Notes

Reaction equation

HRID 2260086 reaction equation
[OH:1][CH:2]([CH2:19][OH:20])[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][CH3:18].[OH-].[K+].[C:23]([O:40]C)(=O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>>[OH:1][CH:2]([CH2:19][OH:20])[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][CH3:18])[C:23](=[O:40])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 3

HCID 8181Methyl PalmitateHCID 14797Potassium HydroxideHCID 189993733-(Tetradecylamino)propane-1,2-diol

Product 1

HCID 15825478N-(2,3-dihydroxypropyl)-N-tetradecylhexadecanamide

Procedure

N-(2,3-dihydroxypropyl)-N-tetradecylamine (1.0 g, 0.0035 moles) and potassium hydroxide (0.01 g, 0.18 mmole) were heated to 85° C. under vacuum. Methyl palmitate (1.036 g, 0.0038 mole) was heated to melt and added dropwise to the reaction. The reaction was heated under vacuum for 6 hours. A waxy off-white solid was obtained (crude yield=1.77 g). The waxy solid was recrystalized from hot hexane (yield=0.33 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=1.77 g)
  4. customThe waxy solid was recrystalized from hot hexane (yield=0.33 g)

Sources & evidence

ORD record
ord-5300df45c4fb43a6ad22a6a7bca87b4e
Source dataset
uspto-grants-1995_12
Patent number
US05476671

Reaction notes

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