Benzoyl chloride → HCID 23361287, compound

HRID 742587Notes

Reaction equation

HRID 742587 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[C:20]([N:10]1[CH2:11][CH2:12][CH2:13][CH:9]1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 36138242-(3-Methoxyphenyl)pyrrolidine

Product 1

HCID 23361287HCID 23361287, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)pyrrolidine (1.0 g) in dry acetonitrile (50 ml) was added milled potassium carbonate (2.0 g) followed by benzoyl chloride (0.73 ml) at ambient temperature, under nitrogen. The reaction mixture was stirred for 2 hrs, filtered through a pad of celite, and the filter cake was washed with ethyl acetate. The combined filtrates were concentrated, and the residue was purified by flash column chromatography (silica gel, 0-25% ethyl acetate/dichloromethane). The appropriate fractions were collected and concentrated to give 1.2 g (75%) of 1-benzoyl-2-(3-methoxyphenyl)pyrrolidine.

Workup

  1. filtrationfiltered through a pad of celite
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated
  4. customthe residue was purified by flash column chromatography (silica gel, 0-25% ethyl acetate/dichloromethane)
  5. customThe appropriate fractions were collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-00db8c5a7d66462ebfbc66e40bafd262
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

Loading…