Potassium Carbonate → HCID 19007305, compound

HRID 1742695Notes

Reaction equation

HRID 1742695 reaction equation
[C:1]([C:4]([CH:17]1[CH2:21][CH2:20][NH:19][CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2].[CH3:22][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]([C:4]([CH:17]1[CH2:21][CH2:20][N:19]([CH2:28][CH2:27][C:26]2[CH:30]=[CH:31][C:23]([CH3:22])=[CH:24][CH:25]=2)[CH2:18]1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5706804-Methylphenethyl bromideHCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 19007305HCID 19007305, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.6 g--see Preparation 8), 4-methylphenethyl bromide (0.44 g), anhydrous potassium carbonate (0.6 g) and acetonitrile (20 ml) was heated under reflux for 1.25 hours. The mixture was partitioned between 10% aqueous potassium carbonate (10 ml) and dichloromethane (20 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 (0% up to 6%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless foam, yield, 0.32 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.25 hours
  3. customThe mixture was partitioned between 10% aqueous potassium carbonate (10 ml) and dichloromethane (20 ml)
  4. customthe layers were 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 a gum which
  9. customwas purified by column chromatography on silica eluting with dichloromethane
  10. additioncontaining methanol (0% up to 6%)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a53c3e257e54a178d1b2be658e31d8f
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

Loading…