Acetonitrile → HCID 19007315, compound

HRID 1742688Notes

Reaction equation

HRID 1742688 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].C(=O)([O-])[O-].[K+].[K+].[C:28](#[N:30])[CH3:29]>O>[C:1]([C:4]([CH:17]1[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][C:4]2[CH:11]=[CH:12][C:29]([C:28]#[N:30])=[CH:6][CH:5]=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 6342AcetonitrileHCID 11430Potassium CarbonateHCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 19007315HCID 19007315, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture contaiing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.6 g--g see Preparation 13), anhydrous potassium carbonate (0.5 g) and acetonitrile (20 ml) was heated under reflux for 1.5 hours. On cooling to room temperature, water (60 ml) was added and the mixture extracted with dichloromethane (3×50 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, 0.25 g.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. extractionthe mixture extracted with dichloromethane (3×50 ml)
  3. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a gum which
  6. customwas purified by column chromatography on silica eluting with dichloromethane
  7. additioncontaining methanol (0% up to 6%)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a75c5b6a1b24daf82b4c05ea9f5fe17
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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