Ethanolamine → 1-(2-Hydroxyethylamino)-2,16-hexadecanediol

HRID 1113

Reaction equation

HRID 1113 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].N#N.[O:7]1[CH: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][CH2:22][CH2:23][OH:24])[CH2:8]1>C(O)C>[OH:2][CH2:1][CH2:3][NH:4][CH2:8][CH:9]([OH:7])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]

Participants

5

Reactant 3

HCID 700Ethanolamine2×HCID 947NitrogenHCID 196946001,2-Epoxy-16-hexadecanol

Product 1

HCID 196946261-(2-Hydroxyethylamino)-2,16-hexadecanediolYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A 50-ml two-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 4.14 g (68 mmol) of ethanolamine and 0.8 g of ethanol. While heating and stirring the mixture at 80° C. in an N2 atmosphere, an ethanol solution of 0.87 g (3.4 mmol) of 1,2-epoxy-16-hexadecanol was added dropwise over 1.5 hours. The resultant mixture was stirred further for 2 hours at 80° C. After completion of the reaction, ethanol and excess ethanolamine were distilled off under reduced pressure, and the resultant residue was purified by flash column chromatography on silica gel, thereby obtaining 0.72 g (yield: 68%) of the title compound (IId-1).

Workup

  1. customA 50-ml two-necked flask equipped with a stirrer
  2. temperatureWhile heating
  3. distillationwere distilled off under reduced pressure
  4. customthe resultant residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-c54f235e113e4ef68f3a56e016403a66
Source dataset
uspto-grants-1998_03
Patent number
US05723497

Linked notes

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