Glycidol → HCID 20089975, compound

HRID 258387Notes

Reaction equation

HRID 258387 reaction equation
[CH2:1]1[O:3][CH:2]1[CH2:4][OH:5].[CH2:6]([NH:13][CH:14]([CH3:18])[CH2:15][C:16]#[N:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[CH2:6]([N:13]([CH:14]([CH3:18])[CH2:15][C:16]#[N:17])[CH2:1][CH:2]([OH:3])[CH2:4][OH:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 11164Glycidol2×HCID 20090032HCID 20090032, compound

Product 1

HCID 20089975HCID 20089975, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of glycidol (70 ml, 1.05 mol) and 3-(benzylamino)butyronitrile (111 g, 0.64 mol) in ethanol (800 ml) was heated to reflux for 18 hours. Additional glycidol (50 ml, 0.75 mol) was added, and the mixture was heated at reflux for an additional 24 hours. Removal of solvent in vacuo left a residue which was partitioned between water and ethyl acetate. The organic layer was washed with water, washed with saturated sodium chloride solution and dried over sodium sulfate. Filtration and concentration in vacuo provided an oil, which was purified by column chromatography (eluant: 5% methanol in chloroform) to give the title product as an oil (42 g, 0.17 mol, 27% yield). 1H NMR (CDCl3) 7.31 (m, 5H), 3.77 (d, J=13.4 Hz, 1H), 3.67 (m, 3H), 3.49 (d, J=13.5 Hz, 1H), 3.43 (m, 1H), 3.18 (m, 1H), 2.55 (m, 4H), 2.30 (m, 1H), 1.16 and 1.08 (d, J=6.5 Hz, 3H).

Workup

  1. temperatureto reflux for 18 hours
  2. temperaturethe mixture was heated
  3. temperatureat reflux for an additional 24 hours
  4. customRemoval of solvent in vacuo
  5. waitleft a residue which
  6. customwas partitioned between water and ethyl acetate
  7. washThe organic layer was washed with water
  8. washwashed with saturated sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. filtrationFiltration and concentration in vacuo
  11. customprovided an oil, which
  12. customwas purified by column chromatography (eluant: 5% methanol in chloroform)

Sources & evidence

ORD record
ord-a89f1a54618e4b7a94d69dc4645dc20f
Source dataset
uspto-grants-1993_11
Patent number
US05266569

Reaction notes

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