4-(2,3-Epoxypropyl)morpholine → 4-(3'-Morpholino-2'-hydroxypropoxy)-3-phenyl-5,6,7,8-tetrahydrocoumarin

HRID 904330Notes

Reaction equation

HRID 904330 reaction equation
[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH:26]2[O:28][CH2:27]2)[CH2:21][CH2:20]1>C(C(C)=O)C(C)C>[O:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH:26]([OH:28])[CH2:27][O:1][C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[O:5][C:4](=[O:12])[C:3]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 977514-(2,3-Epoxypropyl)morpholineHCID 54721330HCID 54721330, compound

Product 1

HCID 233340524-(3'-Morpholino-2'-hydroxypropoxy)-3-phenyl-5,6,7,8-tetrahydrocoumarinYield 77%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A solution of 4-hydroxy-3-phenyl-5,6,7,8-tetrahydrocoumarin and 3-morpholino-1,2-epoxypropane in methyl isobutyl ketone is brought under reflux for 8 hours. Evaporation is carried out under vacuum and the residue is taken up by a 5% solution of sodium bicarbonate and kept for 15 minutes at reflux. After cooling, extraction is carried out with chloroform, drying takes place on sodium sulphate and the chloroform is evaporated. An oil is obtained which cannot be crystallised. Yield 77%.

Workup

  1. temperatureunder reflux for 8 hours
  2. customEvaporation
  3. temperatureat reflux
  4. temperatureAfter cooling
  5. extractionextraction
  6. customdrying
  7. customthe chloroform is evaporated
  8. customAn oil is obtained which
  9. customcannot be crystallised

Sources & evidence

ORD record
ord-126f259361194f169017bd25cb4b9a7d
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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