Ethanolamine → N-(2-hydroxy-3-hexadecyloxypropyl)ethanolamine
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][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:6]1[O:8][CH2:7]1>>[OH:8][CH:6]([CH2:5][O: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][CH2:24][CH3:25])[CH2:7][NH:4][CH2:3][CH2:1][OH:2]Participants
Procedure
61.1 g (1.0 mol) of ethanolamine was introduced into a 200-ml four-necked flask equipped with a stirrer, a dropping funnel, a thermometer and a reflux condenser and heated to 60° to 70° C. under stirring. 24.3 g (0.082 mol) of hexadecyl glycidyl ether was added dropwise thereto over a period of 45 minutes. After the addition was completed, the resulting mixture was heated and stirred under the same conditions as those described above for additional two hours. Then unreacted ethanolamine was distilled off under reduced pressure (79 to 81° C./20 Torr). The residue was purified by silica gel flash column chromatography to thereby give 18.4 g of the compound (IIIa) at a yield of 63%. The data of the 1H-NMR of the obtained compound are as follows:
Workup
- customequipped with a stirrer, a dropping funnel
- temperaturea thermometer and a reflux condenser and heated to 60° to 70° C.
- additionAfter the addition
- temperaturethe resulting mixture was heated
- stirringstirred under the same conditions as
- customthose described above for additional two hours
- distillationThen unreacted ethanolamine was distilled off under reduced pressure (79 to 81° C./20 Torr)
- customThe residue was purified by silica gel flash column chromatography
Sources & evidence
- ORD record
- ord-68730badb9c940ed97e9fa2ce447c2a5
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05221757
Reaction notes
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