Benzyl Chloride → 1-Phenylmethyl-2-(3-methoxyphenyl)pyrrolidine

HRID 1742271Notes

Reaction equation

HRID 1742271 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+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[C:21]1([CH2:20][N:10]2[CH2:11][CH2:12][CH2:13][CH:9]2[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 36138242-(3-Methoxyphenyl)pyrrolidine

Product 1

HCID 233612591-Phenylmethyl-2-(3-methoxyphenyl)pyrrolidineYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)pyrrolidine (3.0 g) in dry acetonitrile (70 ml) was added milled potassium carbonate (3.7 g) followed by benzyl chloride (2.2 g) at ambient temperature, under nitrogen. The reaction mixture was stirred for 5 hrs, warmed under reflux for 2 hrs, and cooled to ambient temperature. The reaction mixture was filtered through a pad of celite, and the solids washed with ethyl acetate. The combined filtrates were concentrated to give 4.3 g (96%) of 1-phenylmethyl-2-(3-methoxyphenyl)pyrrolidine.

Workup

  1. temperaturewarmed
  2. temperatureunder reflux for 2 hrs
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. washthe solids washed with ethyl acetate
  5. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-0aa5fb48c4e5464a8fff1a50bdf18549
Source dataset
uspto-grants-1994_08
Patent number
US05338739

Reaction notes

Loading…