Potassium Carbonate → HCID 19088500, compound

HRID 1587880Notes

Reaction equation

HRID 1587880 reaction equation
Br[CH2:2][CH2:3][C:4]([C:17]#[N:18])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:19][NH:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:17]([C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH2:2][N:20]([CH3:19])[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)#[N:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 35417N-Methyl-3-phenylpropan-1-amineHCID 965754-Bromo-2,2-diphenylbutyronitrile

Product 1

HCID 19088500HCID 19088500, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-bromo-1-cyano-1,1-diphenyl-propane (1.5 g-see Preparation 4), 1-(N-methylamino)-3-phenylpropane (0.746 g), anhydrous potassium carbonate (1.38 g) and acetonitrile (50 ml) was heated under reflux for 48 hours and then concentrated in vacuo. Water (30 ml) was added to the residue and the mixture was extracted with dichloromethane (3×40 ml). The combined dichloromethane extracts were dried (Na2SO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with hexane containing dichloromethane (25% up to 100%) and then dichloromethane containing methanol (0% up to 4%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum, yield, 0.93 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. concentrationconcentrated in vacuo
  4. additionWater (30 ml) was added to the residue
  5. extractionthe mixture was extracted with dichloromethane (3×40 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto give a gum which
  9. customwas purified by column chromatography on silica eluting with hexane
  10. additioncontaining dichloromethane (25% up to 100%)
  11. additiondichloromethane containing methanol (0% up to 4%)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-123aa0454ad44c9b8bd2b53cd99fa9ba
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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