Dimethylformamide → HCID 43190807, compound

HRID 742376Notes

Reaction equation

HRID 742376 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25].C(OCC)(=O)C.C[N:35](C)C=O>O>[C:1]1([CH:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:8]([NH:35][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 737261,1-Diphenylpropane

Product 1

HCID 43190807HCID 43190807, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-1-(3,5-bis(trifiuoromethyl)phenyl)methyloxy)-3,3-diphenylpropane (0.365 g, Example 1f, liberated from its hydrochloride salt by partitioning between ethyl acetate and 10% aqueous sodium carbonate solution followed by drying (MgSO4) and evaporation in vacuo), K2CO3 (0.5 g), and methyl bromacetate (1.23 g) were stirred in dimethyl formamide (5 ml) for 30 minutes. Ethyl acetate (50 ml) and water (50 ml) were added and the organic phase was washed further with water (50 ml), saturated brine (50 ml) and dried (MgSO4). After evaporation the residue was chromatographed on silica gel (eluting with ethyl acetate: hexane (4:6)) to give 1-(3.5-bis(trifiuoromethyl)phenyl)methyloxy)-3,3-diphenyl-2-(N -((carbomethoxy)methyl)amino)propane as an oil.

Workup

  1. washthe organic phase was washed further with water (50 ml), saturated brine (50 ml)
  2. dry with materialdried (MgSO4)
  3. customAfter evaporation the residue
  4. customwas chromatographed on silica gel (eluting with ethyl acetate: hexane (4:6))

Sources & evidence

ORD record
ord-aad92af49c50464586aa6d97207d9029
Source dataset
uspto-grants-1996_09
Patent number
US05554633

Reaction notes

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