Sodium Carbonate → 3-(4-Fluorophenacyl)-1-(2-hydroxyethyl)pyrrolidine

HRID 1461740Notes

Reaction equation

HRID 1461740 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6](=[O:13])[CH2:7][CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:13])[CH2:7][CH:8]2[CH2:12][CH2:11][N:10]([CH2:17][CH2:18][OH:19])[CH2:9]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 110850303-(4-Fluorobenzoylmethyl)pyrrolidine

Product 1

HCID 148827083-(4-Fluorophenacyl)-1-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 30.5 g of 3-(4-fluorophenacyl)pyrrolidine (Chem. Pharm. Bull., 1977, 25(8), p. 1911-1922), 19.4 g of 2-bromoethanol, 15.6 g of sodium carbonate and 400 ml of acetonitrile is heated to reflux for 6 hours. The mixture is concentrated, the residue is taken up in 150 ml of aqueous saline, the product is extracted 5 times with 150 ml of dichloromethane and this organic phase is dried over anhydrous sodium sulfate and concentrated. The oil obtained is purified by chromatography on 650 g of silica (70-230 mesh), using a mixture of dichloromethane, methanol and ammonia solution (96:4:0.4 V/V) as eluant. A colorless oil is obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 6 hours
  3. concentrationThe mixture is concentrated
  4. extractionthe product is extracted 5 times with 150 ml of dichloromethane
  5. dry with materialthis organic phase is dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe oil obtained
  8. customis purified by chromatography on 650 g of silica (70-230 mesh)
  9. additiona mixture of dichloromethane, methanol and ammonia solution (96:4:0.4 V/V) as eluant
  10. customA colorless oil is obtained

Sources & evidence

ORD record
ord-90163f3eb6c34aa0b7597b26a6cc43ae
Source dataset
uspto-grants-1991_12
Patent number
US05077288

Reaction notes

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