Hydrochloric Acid → 1-Methyl-2-{2-[2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine hydrochloride

HRID 743286Notes

Reaction equation

HRID 743286 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OCC)(=O)C.[ClH:30]>O1CCOCC1>[ClH:30].[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 107837421-Methyl-2-{2-[2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine

Product 1

HCID 574976301-Methyl-2-{2-[2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine hydrochlorideYield 24%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 480 mg of 1-methyl-2-{2-[2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine [prepared as described in step (a) above] in a suitable amount of ethyl acetate was treated with 0.5 ml of a 4N solution of hydrogen chloride in dioxane, and the resulting mixture was then concentrated by distillation under reduced pressure. The resulting oily residue was dissolved in 10 ml ethyl acetate, and the solution thus obtained was allowed to stand at room temperature. The crystals which precipitated were collected by filtration, to give 130 mg (yield 24%) of the title compound as colorless needles, melting at 154°-156° C.

Workup

  1. concentrationthe resulting mixture was then concentrated by distillation under reduced pressure
  2. dissolutionThe resulting oily residue was dissolved in 10 ml ethyl acetate
  3. customthe solution thus obtained
  4. customto stand at room temperature
  5. customThe crystals which precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-819b97c415a94c269a7154ab00238d0d
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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