Ethanolamine → 1-(2-Hydroxyethylamino)-2-methyl-3-tetradecyloxy-2-propanol

HRID 1103

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].[O:5]1[C:7]([CH3:24])([CH2:8][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][CH3:23])[CH2:6]1>C(O)C>[OH:2][CH2:1][CH2:3][NH:4][CH2:24][C:7]([CH3:6])([OH:5])[CH2:8][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][CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A 100-ml flask equipped with a stirrer and dropping funnel was then charged with 16.8 g (280 mmol) of ethanolamine and 15 g of ethanol. While stirring the mixture at 80° C., an ethanol solution of 5.00 g (17.6 mmol) of 1,2-epoxy-2-methyl-3-tetradecyloxypropane was added dropwise over 3 hours. The contents were stirred further for 2 hours. The resultant reaction mixture was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 4.13 g (yield: 68%) of the title compound.

Workup

customA 100-ml flask equipped with a stirrer
stirringThe contents were stirred further for 2 hours
customThe resultant reaction mixture
concentrationwas concentrated under reduced pressure
customthe resultant residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-40839e5adad8417b8a69e675e27185ad
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723497

Linked notes

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