Potassium Carbonate → HCID 19088470, compound

HRID 1463888Notes

Reaction equation

HRID 1463888 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]([Cl:29])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][N:20]([CH2:2][CH2:3][C:4]([C:17]#[N:18])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:19])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 135897732-(4-Chlorophenyl)-N-methylethan-1-amine

Product 1

HCID 19088470HCID 19088470, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-bromo-1-cyano-1,1-diphenylpropane (0.9 g--see Preparation 4), N-methyl-4-chlorophenethylamine (0.51 g, see CA 61:15224h), anhydrous potassium carbonate (0.83 g) and acetonitrile (40 ml) was heated under reflux for 24 hours then partitioned between dichloromethane (50 ml) and water (50 ml). The dichloromethane layer was 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 40%) and then with dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum yield, 0.25 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customthen partitioned between dichloromethane (50 ml) and water (50 ml)
  4. dry with materialThe dichloromethane layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give a gum which
  7. customwas purified by column chromatography on silica eluting with hexane
  8. additioncontaining dichloromethane (25% up to 40%)
  9. additionwith dichloromethane containing methanol (0% up to 5%)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa53e56cc15740ecb7aebd260cf28019
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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