HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1115
Notes
Print preview

Reaction equation

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 947NitrogenHCID 14797Potassium HydroxideHCID 19694613N,N-bis(2-hydroxyethyl)-16-hydroxyhexadecanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 2201514616-[N,N-bis(2-hydroxyethyl)amino]-1-hexadecanolYield 62%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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

  1. customA 500-ml flask equipped with a stirrer
  2. temperaturereflux condenser
  3. additionwere added
  4. temperatureAfter cooling the reaction mixture to room temperature
  5. customa salt deposited was separated by filtration
  6. distillationThe solvent was then distilled off under reduced pressure
  7. 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

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes