Isopropanol → Morpholine, 2-[(2-methoxyphenoxy)methyl]-

HRID 1017248Notes

Reaction equation

HRID 1017248 reaction equation
[O:1]1[CH2:13][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12].[NH2:14][CH2:15]COS(O)(=O)=O.[OH-].[K+].[CH:24](O)(C)C>O>[CH3:12][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH:2]1[O:1][CH2:13][CH2:15][NH:14][CH2:24]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 70223Aminoethyl sulfateHCID 98357((o-Methoxyphenoxy)methyl)oxirane

Product 1

HCID 11333552Morpholine, 2-[(2-methoxyphenoxy)methyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2-epoxy-1-(2-methoxyphenoxy)-propane (13.0 g, 72 mmol), 2-aminoethylhydrogensulfate (51 g, 361 mmol), potassium hydroxide (41 g, 722 mmol) in isopropanol (300 ml) and water 100 ml was refluxed for 8 h. Water was added and the product was extracted with two portions of ethylacetate. Drying and evaporation gave a crude product that was used without further purification. Yield 9.2 g.

Workup

  1. temperaturewas refluxed for 8 h
  2. extractionthe product was extracted with two portions of ethylacetate
  3. customDrying
  4. customevaporation

Sources & evidence

ORD record
ord-c9b35cd506c74bdb8f43a9a3d427b97a
Source dataset
uspto-grants-2002_11
Patent number
US06479491B1

Reaction notes

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