Potassium Carbonate → 2,2-diphenyl-5-[N-{2-(2,3-dihydrobenzofur-5-yl)ethyl}-N-methylamino]pentanamide

HRID 1463864Notes

Reaction equation

HRID 1463864 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:26]=[CH:27][C:28]2[O:32][CH2:31][CH2:30][C:29]=2[CH:33]=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]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]3[O:32][CH2:31][CH2:30][C:29]=3[CH:33]=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 190884752,2-Diphenyl-5-methylaminopentanamideHCID 218311605-(2-Bromoethyl)-2,3-dihydro-1-benzofuran

Product 1

HCID 190884782,2-diphenyl-5-[N-{2-(2,3-dihydrobenzofur-5-yl)ethyl}-N-methylamino]pentanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 2,2-diphenyl-5-methylaminopentanamide (0.3--see Preparation 3), 5-(2-bromoethyl)-2,3-dihydrobenzofuran (0.242 g--see Preparation 20), 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 0.26 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-1155e5766dd545d1ab48f294ee09026d
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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