Nitrogen → 12-Hydroxy-N-{2-[(2-hydroxyethyl)amino]ethyl}octadecanamide

HRID 1119

Reaction equation

HRID 1119 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH:5](O)[CH3:6].C[O-:9].[Na+].N#N.[OH:13][CH:14]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=O>C1COCC1.O>[OH:9][CH2:6][CH2:5][NH:4][CH2:3][CH2:2][NH:1][C:25](=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([OH:13])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 947NitrogenHCID 174512Ethanol, 1-((2-aminoethyl)amino)-HCID 345765112-Hydroxystearic acid ethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 1969463912-Hydroxy-N-{2-[(2-hydroxyethyl)amino]ethyl}octadecanamideYield 737.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 30-ml two-necked flask equipped with a stirrer and dropping funnel was charged with 2.08 g (20 mmol) of aminoethylaminoethanol and 0.054 g (1 mmol) of sodium methoxide. While heating and stirring the contents at 80° C. in an N2 atmosphere, a solution of 3.29 g (10 mmol) of ethyl 12-hydroxystearate in 10 ml of THF was added dropwise over 2 hours. The resultant mixture was stirred further for 13 hours at 80° C. under reduced pressure. After completion of the reaction, the reaction mixture was poured into 500 ml of water, and precipitate formed was purified by flash column chromatography on silica gel, thereby obtaining 2.85 g (yield: 74%) of the title compound (IIf-1).

Workup

  1. customA 30-ml two-necked flask equipped with a stirrer
  2. temperatureWhile heating
  3. customAfter completion of the reaction
  4. customformed
  5. customwas purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-4e7d6fabfea64e0cb15c31ea61de1db0
Source dataset
uspto-grants-1998_03
Patent number
US05723497

Linked notes

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