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

HRID 1463858Notes

Reaction equation

HRID 1463858 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.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Br)=[CH:25][CH:24]=1.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]([CH2:28][CH2:27][C:26]2[CH:30]=[CH:31][C:23]([Cl:22])=[CH:24][CH:25]=2)[CH3:15])[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 230291-(2-Bromoethyl)-4-chlorobenzeneHCID 190884752,2-Diphenyl-5-methylaminopentanamide

Product 1

HCID 190884802,2-diphenyl-5-[N-(4-chlorophenethyl)-N-methylamino]pentanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 2,2-diphenyl-5methylaminopentanamide (0.3 g--see Preparation 3), 4-chlorophenethyl bromide (0.234 g--see Preparation 7), anhydrous potassium carbonate (0.4 g) and acetonitrile (10 ml) was heated under reflux for 5 hours. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane (30 ml) and 10% aqueous potassium carbonate (30 ml). The layers were separated and the aqueous layer extracted with dichloromethane (3×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (5% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum, yield 0.306 g.

Workup

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

Sources & evidence

ORD record
ord-99f68429616445159fb740db51b7f098
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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