Acetonitrile → HCID 23170090, compound

HRID 1742692Notes

Reaction equation

HRID 1742692 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][O:23][C:24]([C:26]1[CH:34]=[CH:33][C:29]([CH2:30][CH2:31]Br)=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:1]([C:4]([CH:17]1[CH2:21][CH2:20][N:19]([CH2:31][CH2:30][C:29]2[CH:33]=[CH:34][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:27][CH:28]=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 10586287Methyl 4-(2-bromoethyl)benzoateHCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 23170090HCID 23170090, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.6 g--see Preparation 8), 4-methoxycarbonylphenethyl bromide (0.53 g--see Preparation 15), 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 resulting 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 (2% up to 6%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless foam, yield, 0.44 g.

Workup

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

Sources & evidence

ORD record
ord-304f09de84624e529929c7f46c51d693
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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