Acetonitrile → HCID 19007306, compound

HRID 1742690Notes

Reaction equation

HRID 1742690 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].[O:22]([CH2:29][CH2:30][CH2:31]Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:1]([C:4]([CH:17]1[CH2:21][CH2:20][N:19]([CH2:31][CH2:30][CH2:29][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][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 68522Benzene, (3-bromopropoxy)-HCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 19007306HCID 19007306, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.3 g--see Preparation B), 3-phenoxypropylbromide (0.24 g), anhydrous potassium carbonate (0.4 g) and acetonitrile (10 ml) was heated under reflux for 5 hours. On cooling to room temperature water (40 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 an oil which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 7%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless foam, yield, 0.23 g.

Workup

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

Sources & evidence

ORD record
ord-18a4e15d9a344df598585a3f8159cf0d
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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