Acetonitrile → HCID 19007313, compound

HRID 1742686Notes

Reaction equation

HRID 1742686 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][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[CH2:26][CH2:27]Br.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:1]([C:4]([CH:17]1[CH2:21][CH2:20][N:19]([CH2:27][CH2:26][C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([CH3:22])[CH:24]=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 5706841-(2-Bromoethyl)-3-methylbenzeneHCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 19007313HCID 19007313, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.5 g--see Preparation 8), 3-methylphenethylbromide (0.36 g--see J. Ind. Chem. Sac., 40, 327, (1963)) , anhydrous potassium carbonate (0.5 g) and acetonitrile (10 ml) was heated under reflux for 4 hours. On cooling to room temperature, water (60 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 an oil which was purified by column chromatography on silica eluting with dichloromethane containing methanol (2% up to 4%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield, 0.17 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 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 an oil which
  7. customwas purified by column chromatography on silica eluting with dichloromethane
  8. additioncontaining methanol (2% up to 4%)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f116f3b586c640478f1e75436eda0efd
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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