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

HRID 1463857Notes

Reaction equation

HRID 1463857 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 containing 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).

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)

Sources & evidence

ORD record
ord-b26a5b39d7724422a7f86c18c2029c5e
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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