Acetonitrile → HCID 19088504, compound

HRID 1587882Notes

Reaction equation

HRID 1587882 reaction equation
Br[CH2:2][CH2:3][CH: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.[CH3:17][NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[C:34](#[N:36])C>>[C:34]([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:18]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH3:17])#[N:36]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 883331,1'-(3-Bromopropylidene)bisbenzeneHCID 120234(2-(4-Fluorophenyl)ethyl)(methyl)amine

Product 1

HCID 19088504HCID 19088504, compound

Procedure

A mixture containing 3-bromo-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-6da65775300d4162a351ce8db213b24d
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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