Potassium Iodide → 2,2-diphenyl-5-(N-methyl-N-phenethylamino)pentanamide

HRID 1587849Notes

Reaction equation

HRID 1587849 reaction equation
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][NH:14][CH3:15])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[I-].[K+].[C:33](#N)C>>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][N:14]([CH3:33])[CH2:15][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 2314961-Chloro-2-phenylethaneHCID 190884752,2-Diphenyl-5-methylaminopentanamide

Product 1

HCID 190884792,2-diphenyl-5-(N-methyl-N-phenethylamino)pentanamide

Procedure

A mixture constaining 2,2-diphenyl-5-methylaminopentanamide (0.28 g-see Preparation 3), phenethyl chloride (0.14 g) anhydrous potassium carbonate (0.58 g), anhydrous potassium iodide (0.3 g) and acetonitrile (10 ml) was heated under reflux for 16 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml), the layers separated and the aqueous layer extracted with dichloromethane (2×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting 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 foam, yield 0.14 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×20 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography on silica eluting with dichloromethane
  10. additioncontaining methanol (0% up to 5%)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0a3f6da4d14443e8bcb885476a4f79a
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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