Potassium Carbonate → HCID 19088498, compound

HRID 1463861Notes

Reaction equation

HRID 1463861 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]=[C:27]2[C:31](=[CH:32][CH:33]=1)[CH2:30][CH2:29][CH2:28]2.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]=[C:27]3[C:31](=[CH:32][CH:33]=2)[CH2:30][CH2:29][CH2:28]3)[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 212240805-(2-bromoethyl)-2,3-dihydro-1H-indene

Product 1

HCID 19088498HCID 19088498, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 2,2-diphenyl-5-methylaminopentanamide (0.3 g--see Preparation 3), 5-(2-bromoethyl)indane (0.24 g--see Preparation 6), anhydrous potassium carbonate (0.5 g) and acetonitrile (10 ml) was heated under reflux for 16 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml), the layers separated and the aqueous layer extracted with dichloromethane (2×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromotography on silica eluting with dichloromethane containing methanol (0% up to 6%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a foam, yield 0.23 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×20 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 chromotography on silica eluting with dichloromethane
  10. additioncontaining methanol (0% up to 6%)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7ef4dd0fbe34573b7113b74f0d85602
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

Loading…