Morpholine → 4-(2-(2-Hydroxyethoxy)ethyl)morpholine

HRID 454063Notes

Reaction equation

HRID 454063 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:11]1[CH2:12][CH2:13][N:8]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanol

Product 1

HCID 4584644-(2-(2-Hydroxyethoxy)ethyl)morpholineYield 34.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(2-Chloroethoxy)ethanol (1.25 g, 10 mmol) was added to a mixture of morpholine (2.58 g, 30 mmol) and potassium carbonate (5.5 g, 40 mmol) in acetonitrile (50 ml). The mixture was heated at reflux for 6 hours and then stirred for 18 hours at ambient temperature. The insolubles were removed by filtration and the volatiles were removed from the filtrate by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5 followed by 90/10 and then 80/20) to give 2-(2-morpholinoethoxy)ethanol (600 mg, 34%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hours
  3. customThe insolubles were removed by filtration
  4. customthe volatiles were removed from the filtrate by evaporation
  5. customThe residue was purified by column chromatography
  6. washeluting with methylene chloride/methanol (95/5

Sources & evidence

ORD record
ord-777e93fa2ac44f75a459e9e99359a583
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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