Acetonitrile → HCID 19007310, compound

HRID 1742693Notes

Reaction equation

HRID 1742693 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]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]([CH2:30][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 68526Benzene, (2-bromoethoxy)-HCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 19007310HCID 19007310, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.25 g--see Preparation 8), 2-phenoxyethyl bromide (0.18 g), anhydrous potassium carbonate (0.3 g) and acetonitrile (10 ml) was heated under reflux for 1.5 hours. On cooling to room temperature, water (60 ml) was added and the mixture extracted with dichloromethane (3×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated vacuo to give a foam which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 6%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless foam, yield, 0.18 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. extractionthe mixture extracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  5. concentrationconcentrated vacuo
  6. customto give a foam which
  7. customwas purified by column chromatography on silica eluting with dichloromethane
  8. additioncontaining methanol (0% up to 6%)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5327b3c9afef4c43adafc3fd8fcf561a
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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