Morpholine → HCID 3794238, compound

HRID 1458538Notes

Reaction equation

HRID 1458538 reaction equation
Cl[CH2:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+]>>[O:18]1[CH2:19][CH2:20][N:15]([CH2:2][CH:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:16][CH2:17]1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 13948363HCID 13948363, compound2×

Product 1

HCID 3794238HCID 3794238, compoundYield 53.2%

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 3-chloro-2-phenylpropionate (1 g, 4.72 mmol) prepared in the above (1) and morpholine (470 mg, 5.4 mmol) was stirred to cause reaction for 6 hours under heating at 110° C. To the resulting solution, saturated aqueous sodium bicarbonate was added. After the prepared solution was extracted with ethyl ether, the extract was washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. Subsequently, the solvent was removed by distillation under reduced pressure to obtain a crude product. The product was purified by silica gel column chromatography using acetone/hexane=1/6 to obtain 660 mg of the titled compound as a colorless oil (yield: 53.2%).

Workup

  1. customreaction for 6 hours
  2. extractionAfter the prepared solution was extracted with ethyl ether
  3. washthe extract was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSubsequently, the solvent was removed by distillation under reduced pressure
  6. customto obtain a crude product
  7. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40abf8f530674fb08d31a9c4e77819dc
Source dataset
uspto-grants-1998_12
Patent number
US05852006

Reaction notes

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