Ethanolamine → Ammonium Hydroxide

HRID 915659Notes

Reaction equation

HRID 915659 reaction equation
[H-].[Na+].[OH:3]CC[NH2:6].ClC1[CH:13]=[CH:12][CH:11]=[CH:10]N=1.O1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>O.C(Cl)Cl>[NH4+:6].[OH-:3].[O:17]([CH2:18][CH2:19][NH2:6])[C:16]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:15]=1

Participants

8

Reactant 4

HCID 700EthanolamineHCID 79772-ChloropyridineHCID 24758Sodium hydrideHCID 312751,4-Dioxane

Product 2

HCID 14923Ammonium HydroxideHCID 156512-Phenoxyethanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Add sodium hydride (60% in mineral oil, 6.63 g, 166 mmol) to a solution of 2-hydroxyethylamine (10.0 mL, 166 mmol) in dioxane (150 mL), at room temperature under nitrogen. Stir for 10 minutes at room temperature. Add 2-chloropyridine (15.6 mL, 166 mmol) and heat the reaction mixture to reflux. After stirring at reflux for 14 hours, cool the reaction mixture to room temperature and dilute with water (100 mL), and methylene chloride (200 mL). Extract the aqueous layer with methylene chloride (2×100 mL). Combine the organic layers with brine (200 mL), dry (magnesium sulfate), filter and concentrate to an orange oil. Perform flash chromatography on silica gel eluting with 50% of a 80:18:2 CHCl3/MeOH/concentrated NH4OH) solution in methylene chloride to afford the title compound as a yellow oil (17.9 g). MS: m/z=139 (MH+).

Workup

  1. customat room temperature
  2. temperatureto reflux
  3. stirringAfter stirring
  4. temperatureat reflux for 14 hours
  5. temperaturecool the reaction mixture to room temperature
  6. extractionExtract the aqueous layer with methylene chloride (2×100 mL)
  7. dry with materialCombine the organic layers with brine (200 mL), dry (magnesium sulfate)
  8. filtrationfilter
  9. concentrationconcentrate to an orange oil

Sources & evidence

ORD record
ord-eb5171cabcd04f43997e05b9eebcfb71
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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