1-Amino-3-phenylpropan-2-ol → 5-{4-[2-(3-Phenyl-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dione

HRID 2294280Notes

Reaction equation

HRID 2294280 reaction equation
[C:1]1([CH2:7][CH:8]([OH:11])[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:13]([CH3:30])[CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[S:25][C:24](=[O:26])[NH:23][C:22]2=[O:27])=[CH:18][CH:17]=1>C1C=CC=CC=1>[C:1]1([CH2:7][CH:8]([OH:11])[CH2:9][NH:10][CH:13]([CH3:30])[CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:28][CH:29]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 37580461-Amino-3-phenylpropan-2-olHCID 218321505-[4-(2-Oxopropoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 98019075-{4-[2-(3-Phenyl-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dioneYield 39.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

550 mg of 3-phenyl-2-hydroxypropylamine (prepared as described in Preparation 17) and 1.0 g of 5-[4-(2-oxo-propoxy)benzyl]thiazolidine-2,4-dione were suspended in 30 ml of anhydrous benzene, and the resulting suspension was heated under reflux for 30 minutes while removing water. Subsequently, the solvent was removed by evaporation under reduced pressure. The resulting oily product was dissolved in 20 ml of anhydrous methanol, 670 mg of sodium cyanoborohydride was added to the solution, whilst ice-cooling, and the mixture was stirred for 2 hours in a stream of nitrogen gas. After this, the reaction mixture was left to stand overnight, and then the solvent was removed by evaporation under reduced pressure. Water was added to the resulting residue, which was then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed from the extract by evaporation under reduced pressure, and the resulting residue was applied to a silica gel chromatography column, which was eluted with a 5:1 by volume mixture of ethyl acetate and ethanol, and crystallized from ethyl acetate, to give 590 mg of the title compound, melting at 145° C. to 152° C.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureunder reflux for 30 minutes
  3. customwhile removing water
  4. customSubsequently, the solvent was removed by evaporation under reduced pressure
  5. dissolutionThe resulting oily product was dissolved in 20 ml of anhydrous methanol
  6. addition670 mg of sodium cyanoborohydride was added to the solution, whilst ice-
  7. temperaturecooling
  8. waitAfter this, the reaction mixture was left
  9. waitto stand overnight
  10. customthe solvent was removed by evaporation under reduced pressure
  11. additionWater was added to the resulting residue, which
  12. extractionwas then extracted with ethyl acetate
  13. washThe extract was washed with a saturated aqueous solution of sodium chloride
  14. dry with materialdried over anhydrous sodium sulfate
  15. customThe solvent was removed from the
  16. extractionextract by evaporation under reduced pressure
  17. washwas eluted with a 5:1 by volume mixture of ethyl acetate and ethanol
  18. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-03f9fb2fbf1445b68e6bff96c098aa6b
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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