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Ethanolamine → 1-(2-Hydroxyethylamino)-3-[10-(2-ethylhexyloxy)decyloxy]-2-propanol

HRID 1098
Notes
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Reaction equation

HRID 1098 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH2:5]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])[CH:6]1[O:8][CH2:7]1>C(O)C>[OH:2][CH2:1][CH2:3][NH:4][CH2:7][CH:6]([OH:8])[CH2:5][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 700EthanolamineHCID 1969463510-(2-Ethylhexyloxy)decyl glycidyl ether

Product 1

HCID 98659041-(2-Hydroxyethylamino)-3-[10-(2-ethylhexyloxy)decyloxy]-2-propanolYield 68.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 200-ml two-necked flask equipped with a stirrer, reflux tube and dropping funnel was charged with 32.7 g (0.54 mol) of ethanolamine and 10.1 g of ethanol. While heating and stirring the mixture at 80° C., 1.76 g (5.14 mmol) of 10-(2-ethylhexyloxy)decyl glycidyl ether were added dropwise over 2 hours. After the resultant mixture was heated and stirred further for 18 hours, it was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 1.42 g (yield: 68%) of the title compound (Ia-14).

Workup

  1. customA 200-ml two-necked flask equipped with a stirrer
  2. temperaturereflux tube
  3. temperatureWhile heating
  4. stirringstirred further for 18 hours
  5. concentrationit was concentrated under reduced pressure
  6. customthe resultant residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ad4349523f614af097d0bd73d457fcbf
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723497

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes