Potassium Carbonate → HCID 19746810, compound

HRID 2253891Notes

Reaction equation

HRID 2253891 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].[CH2:22]1[O:32][C:31]2[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][C:24]=2[O:23]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:4]([CH:17]1[CH2:21][CH2:20][N:19]([CH2:27][C:26]2[CH:29]=[CH:30][C:31]3[O:32][CH2:22][O:23][C:24]=3[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 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 19746810HCID 19746810, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.75 g-see Preparation 8), 3,4-methylenedioxybenzyl chloride (0.51 g-commercially available), anhydrous potassium carbonate (0.75 g) and acetonitrile (30 ml) was stirred at room temperature for 30 minutes. The mixture was partitioned between 10% aqueous potassium carbonate (20 ml) and dichloromethane (50 ml), the layers were separated and the aqueous layer extracted with dichloromethane (3×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a foam which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a foam, yield 0.5 g.

Workup

  1. customThe mixture was partitioned between 10% aqueous potassium carbonate (20 ml) and dichloromethane (50 ml)
  2. customthe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a foam which
  7. customwas purified by column chromatography on silica eluting with dichloromethane
  8. additioncontaining methanol (0% up to 10%)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e20d7f49b9ca4037bff2f3083e326da2
Source dataset
uspto-grants-1993_08
Patent number
US05233053

Reaction notes

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