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Potassium Carbonate → 2,2-diphenyl-5-[N-(4-cyanophenethyl)-N-methylamino]pentanamide

HRID 1463860
Notes
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Reaction equation

HRID 1463860 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:22]([C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29]Br)=[CH:26][CH:25]=1)#[N:23].C(=O)([O-])[O-].[K+].[K+]>C(#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]([CH2:29][CH2:28][C:27]2[CH:31]=[CH:32][C:24]([C:22]#[N:23])=[CH:25][CH:26]=2)[CH3:15])[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 128865484-(2-Bromoethyl)benzonitrileHCID 190884752,2-Diphenyl-5-methylaminopentanamide

Product 1

HCID 190884772,2-diphenyl-5-[N-(4-cyanophenethyl)-N-methylamino]pentanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 2,2-diphenyl-5-methylaminopentanamide (1.0 g--see Preparation 3), 4-cyanophenethyl bromide (0.82 g), anhydrous potassium carbonate (2.0 g) and acetonitrile (30 ml) was heated under reflux for 10 hours. The mixture was partitioned between dichloromethane (50 ml) and 10% aqueous sodium carbonate (30 ml), the layers separated and the aqueous layer extracted with dichloromethane (2×30 ml). The combined dichloromethane extracts were dried (MgSO2) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 6%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was further purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 4%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield 0.22 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. customThe mixture was partitioned between dichloromethane (50 ml) and 10% aqueous sodium carbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×30 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO2)
  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 6%)
  11. concentrationconcentrated in vacuo
  12. customto give an oil which
  13. customwas further purified by column chromatography on silica eluting with dichloromethane
  14. additioncontaining methanol (0% up to 4%)
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-409e147051da4e9dad9101cee41e1f5e
Source dataset
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05302595

Reaction notes

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