Potassium Carbonate → HCID 19088471, compound

HRID 1587860Notes

Reaction equation

HRID 1587860 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.Br[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:27][CH:26]=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]([CH3:15])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:27][CH:26]=2)[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12870363HCID 12870363, compoundHCID 190884752,2-Diphenyl-5-methylaminopentanamide

Product 1

HCID 19088471HCID 19088471, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 2,2-diphenyl-5-methylaminopentanamide (0.56 g-see Preparation 3), methyl 4-(2-bromoethyl)phenylacetate (0.51 g-see Preparation 22), anhydrous potassium carbonate (0.6 g) and acetonitrile (20 ml) was heated under reflux for 5.5 hours. The mixture was partitioned between dichloromethane (70 ml) and 10% aqueous potassium carbonate (50 ml), the layers separated, and the aqueous layer extracted with dichloromethane (2×50 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 hexane (50%) then with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield 0.2 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5.5 hours
  3. customThe mixture was partitioned between dichloromethane (70 ml) and 10% aqueous potassium carbonate (50 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×50 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a gum which
  9. customwas purified by column chromatography on silica eluting with dichloromethane
  10. additioncontaining hexane (50%)
  11. additionwith dichloromethane containing methanol (0% up to 10%)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fcdff0261b94d8f84396be66e151ab4
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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