Acetonitrile → HCID 19746804, compound

HRID 2371871Notes

Reaction equation

HRID 2371871 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:33][C:32]2[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Br)=[CH:25][C:24]=2[O:23]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[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:32]3[O:33][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

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 122072243,4-Methylenedioxyphenethyl bromideHCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 19746804HCID 19746804, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.3 g--see Preparation 8), 3,4-methylenedioxyphenethyl bromide (0.247 g--see Preparation 16), anhydrous potassium carbonate (0.4 g) and acetonitrile (10 ml) was heated under reflux for 3 hours. The mixture was allowed to cool to room temperature, water (6 ml) was added and the mixture was extracted with dichloromethane (3×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a colourless foam 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 0.27 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. extractionthe mixture was extracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a colourless foam which
  7. customwas purified by column chromatography on silica eluting with dichloromethane
  8. additioncontaining methanol (0% up to 6%)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-066084ebe28d451e8f08ffc9845b9921
Source dataset
uspto-grants-1992_03
Patent number
US05096890

Reaction notes

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