Benzene → HCID 9884753, compound

HRID 1953239Notes

Reaction equation

HRID 1953239 reaction equation
C1C=CC=CC=1.[NH2:7][CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[OH:10].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH2:28][C:29]([CH3:31])=O)[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]>O>[Cl:17][C:13]1[CH:12]=[C:11]([C@@H:9]([OH:10])[CH2:8][NH:7][C@H:29]([CH3:31])[CH2:28][C:22]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:20]([O:19][CH3:18])[CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 698962-Propanone, 1-(3,4-dimethoxyphenyl)-HCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanol

Product 1

HCID 9884753HCID 9884753, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 40 ml benzene solution of (R)-2-amino-1-(3-chlorophenyl)ethanol (0.304 g), was added 0.344 g of methyl 3,4-dimethoxyphenylmethyl ketone. The mixture was refluxed in an apparatus equipped with a water-trap for one hour and the water produced was removed from the reaction system. After cooling the reaction mixture, the solvent was distilled off under reduced pressure, and the residue was dissolved into 10 ml of methanol. To the mixture was added platinum oxide, and the reducing reaction was conducted at room temperature at 1 atm pressure under hydrogen atmosphere for 24 hours. After removing off platinum oxide by filtration, the solvent was distilled off under reduced pressure to give 0.501 g of white oil of (R,R)-1-(3-chlorophenyl)-2-[[2-(3,4-dimethoxyphenyl)-1-methylethyl]amino]ethanol (yield 81.0%). The optical purity of the (R,R)-isomer was 80%.

Workup

  1. temperatureThe mixture was refluxed in an apparatus
  2. customequipped with a water-trap for one hour
  3. customwas removed from the reaction system
  4. temperatureAfter cooling the reaction mixture
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionthe residue was dissolved into 10 ml of methanol
  7. additionTo the mixture was added platinum oxide
  8. customthe reducing reaction
  9. customAfter removing off platinum oxide
  10. filtrationby filtration
  11. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-42522cefe38949b6ae5fa1b96fce34cf
Source dataset
uspto-grants-2000_09
Patent number
US06114582

Reaction notes

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