Nitrogen → 2-(9-Octadecenylamino)-1-ethanol

HRID 1111

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].N#N.[C:9]([NH:28][CH2:29][CH2:30][OH:31])(=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[K+]>O1CCCC1>[CH2:9]([NH:28][CH2:29][CH2:30][OH:31])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

A 100-ml eggplant type flask equipped with a stirrer was charged with 1.40 g (37.2 mmol) of LiAlH4 and 30 ml of tetrahydrofuran. While heating and stirring the contents at room temperature in an N2 atmosphere, a tetrahydrofuran solution of 1.67 g (5.12 mmol) of N-(9-octadecenoyl)ethanolamine was added dropwise over 10 minutes. After the mixture was heated to 60° C. and stirred for 16 hours, the resultant reaction mixture was cooled to room temperature, and 14 g of 5% aqueous KOH. After a salt deposited was separated by filtration, the filtrate was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 0.96 g (yield: 65%) of the title compound (IIc-6).

Workup

customA 100-ml eggplant type flask equipped with a stirrer
temperatureWhile heating
customthe resultant reaction mixture
temperaturewas cooled to room temperature
customAfter a salt deposited was separated by filtration
concentrationthe filtrate was concentrated under reduced pressure
customthe resultant residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-70a4eebe93b24ba3bd4111e18405dbfa
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723497

Linked notes

Loading…