Nitrogen → 16-[N,N-bis(2-hydroxyethyl)amino]-1-hexadecanol

HRID 1115

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].N#N.[OH:9][CH2:10][CH2:11][N:12]([CH2:31][CH2:32][OH:33])[C:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29].[OH-].[K+]>O1CCCC1>[OH:33][CH2:32][CH2:31][N: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][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[CH2:11][CH2:10][OH:9]

Participants

Conditions

Temperature: 65 °C

Procedure

A 500-ml flask equipped with a stirrer and reflux condenser was charged with 3.01 g (79.3 mmol) of LiAlH4 and 200 ml of tetrahydrofuran. While stirring the mixture at room temperature in an N2 atmosphere, 5.00 g (13.9 mmol) of N,N-bis(2-hydroxyethyl)-16-hydroxyhexadecanamide were added, followed by stirring at 65° C. for 18 hours. After cooling the reaction mixture to room temperature, 15 g of 3% aqueous KOH were added, and a salt deposited was separated by filtration. The solvent was then distilled off under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 2.98 g (yield: 62%) of the title compound (IId-3).

Workup

customA 500-ml flask equipped with a stirrer
temperaturereflux condenser
additionwere added
temperatureAfter cooling the reaction mixture to room temperature
customa salt deposited was separated by filtration
distillationThe solvent was then distilled off under reduced pressure
customthe resultant residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-f7c05078e24046a8887d238bff8b0c4f
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723497

Linked notes

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