Potassium Iodide → 1-[3-(Diphenylmethoxy)propyl] 3-(3-methoxyphenyl)pyrrolidine

HRID 1032337Notes

Reaction equation

HRID 1032337 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][CH2:9][CH2:10][CH2:11]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]2[CH2:31][CH2:30][NH:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][CH2:9][CH2:10][CH2:11][N:29]2[CH2:30][CH2:31][CH:27]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([O:20][CH3:19])[CH:22]=3)[CH2:28]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 129379913-(3-Methoxyphenyl)pyrrolidineHCID 143063671-(Diphenylmethoxy)-3-bromopropane

Product 1

HCID 145563091-[3-(Diphenylmethoxy)propyl] 3-(3-methoxyphenyl)pyrrolidineYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 5.3 g (50 mmole) of 1-(diphenylmethoxy)-3-bromopropane in 50 cm3 of dimethylformamide was added to a mixture of 8.8 g (50 mmole) of 3-(3-methoxyphenyl)pyrrolidine, 13.8 g (100 mmole) of potassium carbonate, a few potassium iodide crystals and 250 cm3 of dimethylformamide. The reactive medium was heated to 80° C. for 12 hours and then filtered after it returned to room temperature. The filtrate was concentrated to dryness under reduced pressure. The residue was taken up with ether and extracted with 500 cm3 of N hydrochloric acid. The aqueous phase was separated, basified with 10N sodium hydroxide solution and extracted with methylene chloride. The organic solution was dried on sodium sulfate. Evaporation of the solvent yielded an oily residue, which was purified by silica gel column filtration (eluent, hexane-ethyl acetate, 1/1). There was obtained 10.3 g (yield: 51.3%) of 1-[3-(diphenylmethoxy)propyl] 3-(3-methoxyphenyl)pyrrolidine.

Workup

  1. filtrationfiltered after it
  2. customreturned to room temperature
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. extractionextracted with 500 cm3 of N hydrochloric acid
  5. customThe aqueous phase was separated
  6. extractionextracted with methylene chloride
  7. customThe organic solution was dried on sodium sulfate
  8. customEvaporation of the solvent
  9. customyielded an oily residue, which
  10. filtrationwas purified by silica gel column filtration (eluent, hexane-ethyl acetate, 1/1)

Sources & evidence

ORD record
ord-ffb1ceabd32a4e57b42e4156244a95cc
Source dataset
uspto-grants-1990_09
Patent number
US04957927

Reaction notes

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