Water → HCID 22723933, compound

HRID 1460949Notes

Reaction equation

HRID 1460949 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:9](Cl)(=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O>O1CCCC1>[O:21]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8166Dodecanoyl chlorideHCID 24758Sodium hydride

Product 1

HCID 22723933HCID 22723933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2.30g (57.0 mmol) of sodium hydride (60% oil dispersion) in dry tetrahydrofuran (THF) and 5.0 g (57.0 mmol) of morpholine was refluxed under nitrogen for 30 minutes. After cooling, 12.56 g (57.0 mmol) of dodecanoyl chloride in THF was added dropwise, and the mixture was refluxed 30 minutes. Water was added, and the mixture was extracted with ethyl acetate (EtOAc). The combined organic phase was dried with MgSO4, concentrated in vacuo, and purified by flash chromatography (8:1 hexane/EtOAc) to give N-(oxododecyl)morpholine, as confirmed by NMR & IR spectroscopy.

Workup

  1. temperaturewas refluxed under nitrogen for 30 minutes
  2. temperatureAfter cooling
  3. temperaturethe mixture was refluxed 30 minutes
  4. extractionthe mixture was extracted with ethyl acetate (EtOAc)
  5. dry with materialThe combined organic phase was dried with MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (8:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-1336a4c400e540a5900b2d11608df735
Source dataset
uspto-grants-1991_12
Patent number
US05073544

Reaction notes

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