Water → HCID 9907760, compound

HRID 1901151Notes

Reaction equation

HRID 1901151 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4].O=[C:13]([CH3:27])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=1.O>C1C=CC=CC=1>[CH3:26][O:25][C:23]([CH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH:13]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)[OH:4])[CH3:27])=[CH:21][CH:20]=1)=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Product 1

HCID 9907760HCID 9907760, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2.2 g of 2-amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 8) and 2.6 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3) in 200 ml of benzene was heated under reflux for about 2 hours, whilst the water being formed during the reaction was continuously removed. At the end of this time, the reaction mixture was freed from the benzene used as solvent by distillation under reduced pressure, and the resulting residue was dissolved in 150 ml of absolute methanol. 1 g of sodium borohydride was added to this solution, whilst ice-cooling, and the resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was then mixed with ethyl acetate and with a saturated aqueous solution of sodium chloride. The organic layer was separated and was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 40:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine as the eluent, to give 2.3 g of the title compound having an Rf=0.44 (thin layer chromatography over silica gel, using a 40:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine as the developing solvent).

Workup

  1. customformed during the reaction
  2. customwas continuously removed
  3. distillationused as solvent by distillation under reduced pressure
  4. dissolutionthe resulting residue was dissolved in 150 ml of absolute methanol
  5. addition1 g of sodium borohydride was added to this solution, whilst ice-
  6. temperaturecooling
  7. additionThe reaction mixture was then mixed with ethyl acetate and with a saturated aqueous solution of sodium chloride
  8. customThe organic layer was separated
  9. dry with materialwas dried over anhydrous magnesium sulfate
  10. customthe solvent was removed by distillation under reduced pressure
  11. customThe resulting residue was purified by column chromatography through silica gel
  12. additionby volume mixture of ethyl acetate, ethanol and triethylamine as the eluent

Sources & evidence

ORD record
ord-c0dfc88c203a41cda6de08e24c54e077
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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