Potassium Carbonate → HCID 19088504, compound

HRID 1463889Notes

Reaction equation

HRID 1463889 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][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=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]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH3:19])#[N:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 120234(2-(4-Fluorophenyl)ethyl)(methyl)amine

Product 1

HCID 19088504HCID 19088504, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-bromo-1-cyano-1,1-diphenylpropane (1.5 g)--see Preparation 4), N-methyl-4-fluorophenethylamine (0.766 g--see CA 80:PIZ0985y), anhydrous potassium carbonate (1.38 g) and acetonitrile (50 ml) was heated under reflux for 24 hours then concentrated in vacuo. The residue was dissolved in water (40 ml) and extracted with dichloromethane (3×50 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 with dichloromethane containing methanol (0% up to 3%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum, yield, 0.51 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. concentrationthen concentrated in vacuo
  4. dissolutionThe residue was dissolved in water (40 ml)
  5. extractionextracted with dichloromethane (3×50 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. additionwith dichloromethane containing methanol (0% up to 3%)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f15254b28da949bb8b33f8ddf903dca1
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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