Acetonitrile → HCID 19007316, compound

HRID 1742684Notes

Reaction equation

HRID 1742684 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][C:31]=1[CH3:32])[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][C:31]([CH3:32])=[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 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamideHCID 225073204-(2-Bromoethyl)-1,2-dimethylbenzene

Product 1

HCID 19007316HCID 19007316, 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), 3,4-dimethylphenethyl bromide (0.4 g--see Preparation 18), anhydrous potassium carbonate (0.5 g) and acetonitrile (10 ml) was heated under reflux for 2 hours. On cooling to room temperature, water (80 ml) was added and the mixture was extracted with dichloromethane (3×70 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a yellow oil which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 4%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield, 0.22 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. extractionthe mixture was extracted with dichloromethane (3×70 ml)
  4. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil which
  7. customwas purified by column chromatography on silica eluting with dichloromethane
  8. additioncontaining methanol (0% up to 4%)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c079336a170d43f9a11eef2160f1e429
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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