Morpholine → HCID 14882494, compound

HRID 486055Notes

Reaction equation

HRID 486055 reaction equation
[C:1]([OH:13])(=O)[CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[OH:7][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][C:1]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[CH:11]=[CH:10][C:8]=1[OH:9]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 348154Dihydrocaffeic acid

Product 1

HCID 14882494HCID 14882494, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g of dihydrocaffeic acid and 1.43 g of morpholine were dissolved in 20 ml of DMF (dimethylformamide), and 202 mg of DMAP (dimethylaminopyridine) and 3.4 g of DCC (dicyclohexylcarbodiimide) were further added thereto under cooling, followed by allowing the mixture to stand overnight. The deposited dicyclohexyl urea was removed therefrom by filtration, and the resultant filtrate was then distilled off under reduced pressure. Afterward, the residue was washed with ether in order to obtain 3.8 g of N-[3-(3,4-dihydroxyphenyl)propionyl]morpholine in the state of light yellow crystals having a melting point of from 211° to 213° C.

Workup

  1. temperatureunder cooling
  2. customThe deposited dicyclohexyl urea was removed
  3. filtrationby filtration
  4. distillationthe resultant filtrate was then distilled off under reduced pressure
  5. washAfterward, the residue was washed with ether in order

Sources & evidence

ORD record
ord-26e3d672d04b433080b72a5fb90b59f9
Source dataset
uspto-grants-1994_03
Patent number
US05290793

Reaction notes

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