Ethanolamine → N-(2-hydroxyethyl)-N-(2-hexyl-2-hydroxyethyl)amine

Reaction equation

[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2]1.[CH2:10]([CH2:12][NH2:13])[OH:11]>>[OH:11][CH2:10][CH2:12][NH:13][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[OH:1]

Participants

Reactant 2

HCID 700Ethanolamine

HCID 181262-Hexyloxirane

Product 1

HCID 19936261N-(2-hydroxyethyl)-N-(2-hexyl-2-hydroxyethyl)amineYield 93%

Procedure

50 g (0.39 mmole) of 1,2-epoxy-octane are added dropwise to 250 cm3 (4 moles) of ethanolamine at 100° C. Heating is maintained for 1 h after the addition is complete, then the excess ethanolamine is distilled in a vacuum. The residue is recrystallised from 600 cm3 of hexane, after filtration and drying. The solid residue obtained weighs 69 g (melting point 45° C., yield=93% Rf=0.62 silica/butanol/H2O/acetic acid/50/25/11).

Workup

temperatureHeating
temperatureis maintained for 1 h
additionafter the addition
distillationthe excess ethanolamine is distilled in a vacuum
customThe residue is recrystallised from 600 cm3 of hexane
filtrationafter filtration
customdrying
customThe solid residue obtained

Sources & evidence

ORD record: ord-268503a4e4a24e7ab9db3468d77580f8
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05049667

Reaction notes

Loading…