Potassium Carbonate → 1-[2-(4-Bromo-2-methylphenoxy)ethyl]pyrrolidine

HRID 1387057Notes

Reaction equation

HRID 1387057 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.Cl.Cl[CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:14]1([CH2:13][CH2:12][O:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[CH3:9])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 168964-Bromo-2-methylphenolHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 8032231-[2-(4-Bromo-2-methylphenoxy)ethyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-2-methylphenol (10 g, 53.5 mmol) and 1-(2-chloroethyl)pyrrolidine HCl (11 g, 64.7 mmol) were heated at 80° C. in 500 mL of DMF in the presence of K2CO3 (22 g, 159.2 mmol) for 16 h. After cooling, the crude product was filtered and concentrated in vacuo. The brown oily residue was purified by PrepLC (SiO2; gradient of 90:8:2 to 85:10:5 hexanes-THF-TEA) to afford 11.25 g (39.6 mmol; 74%) of the title compound as a clear, colorless oil.

Workup

  1. temperatureAfter cooling
  2. filtrationthe crude product was filtered
  3. concentrationconcentrated in vacuo
  4. customThe brown oily residue was purified by PrepLC (SiO2; gradient of 90:8:2 to 85:10:5 hexanes-THF-TEA)

Sources & evidence

ORD record
ord-d2d91f4d47da4f238c4b57bd781218a2
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

Loading…