Acetonitrile → 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)-1-[2-(1,4-benzodioxan-6-yl)ethyl]pyrrolidine

HRID 2371873Notes

Reaction equation

HRID 2371873 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].Br[CH2:23][CH2:24][C:25]1[CH:34]=[CH:33][C:28]2[O:29][CH2:30][CH2:31][O:32][C:27]=2[CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:1]([C:4]([CH:17]1[CH2:21][CH2:20][N:19]([CH2:23][CH2:24][C:25]2[CH:34]=[CH:33][C:28]3[O:29][CH2:30][CH2:31][O:32][C:27]=3[CH:26]=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 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamideHCID 190885086-(2-Bromoethyl)-2,3-dihydro-1,4-benzodioxin

Product 1

HCID 197468113-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)-1-[2-(1,4-benzodioxan-6-yl)ethyl]pyrrolidine

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), 6-(2-bromoethyl)-1,4-benzodioxan (0.26 g--see Preparation 21), anhydrous potassium carbonate (0.4 g) and acetonitrile (10 ml) was heated under reflux for 3 hours. On cooling to room temperature, water (40 ml) was added and the mixture was extracted with dichloromethane (3×30 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 colourless foam, yield, 0.21 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. extractionthe mixture was extracted with dichloromethane (3×30 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-feb6f498224948d98b4b3ba45295b1f7
Source dataset
uspto-grants-1992_03
Patent number
US05096890

Reaction notes

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