Phenethyl bromide → HCID 23361279, compound

HRID 1742264Notes

Reaction equation

HRID 1742264 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.Br[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 36138242-(3-Methoxyphenyl)pyrrolidine

Product 1

HCID 23361279HCID 23361279, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)pyrrolidine (1.04 g) in dry acetonitrile (30 ml) was added 2-bromoethylbenzene (0.96 ml) followed by milled potassium carbonate (1.78 g) at ambient temperature, under nitrogen. The reaction mixture was stirred for 48 hrs, warmed under reflux for 2 hrs, and cooled to ambient temperature. The reaction mixture was 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, dichloromethane/0-100% ether). The appropriate fractions were collected and concentrated to afford 1.2 g (72%) of 2-(3-methoxyphenyl)-1-(2-phenylethyl)pyrrolidine.

Workup

  1. temperaturewarmed
  2. temperatureunder reflux for 2 hrs
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. washthe filter cake was washed with ethyl acetate
  5. concentrationThe combined filtrates were concentrated
  6. customthe residue was purified by flash column chromatography (silica gel, dichloromethane/0-100% ether)
  7. customThe appropriate fractions were collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-993ad4f64d144df59758647db97c8f46
Source dataset
uspto-grants-1994_08
Patent number
US05338739

Reaction notes

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