Potassium Carbonate → 2,2-diphenyl-5-[N-{2-(1,4-benzodioxan-6-yl)ethyl}-N-methylamino]pentanamide

HRID 1587847Notes

Reaction equation

HRID 1587847 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:34]=[CH:33][C:28]2[O:29][CH2:30][CH2:31][O:32][C:27]=2[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]([CH2:23][CH2:24][C:25]2[CH:34]=[CH:33][C:28]3[O:29][CH2:30][CH2:31][O:32][C:27]=3[CH:26]=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 190885086-(2-Bromoethyl)-2,3-dihydro-1,4-benzodioxin

Product 1

HCID 190885112,2-diphenyl-5-[N-{2-(1,4-benzodioxan-6-yl)ethyl}-N-methylamino]pentanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 2,2-diphenyl-5-methylaminopentanamide (0.36 g-see Preparation 1), 6-(2-bromoethyl)-1,4-benzodioxan (0.32 g), anhydrous potassium carbonate (0.75 g) and acetonitrile (20 ml) was heated under reflux for 16 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 (3×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give a foam which was further purified by column chromatography on alumina eluting with dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a foam, yield 0.11 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 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 (3×20 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  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 5%)
  11. concentrationconcentrated in vacuo
  12. customto give a foam which
  13. customwas further purified by column chromatography on alumina eluting with dichloromethane
  14. additioncontaining methanol (0% up to 5%)
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dca48ea5fd4441f298830488644d869c
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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