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

HRID 743296Notes

Reaction equation

HRID 743296 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25].C(OCC)(=O)C>O1CCOCC1>[ClH:1].[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 194239651-Methyl-2-(2-{2-[2-(2-methylphenyl)ethyl]phenoxy}ethyl)pyrrolidine

Product 1

HCID 194240341-Methyl-2-(2-{2-[2-(2-methylphenyl)ethyl]phenoxy}ethyl)pyrrolidine hydrochlorideYield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.3 ml of a 4N solution of hydrogen chloride in dioxane was added to a solution of 350 mg of 1-methyl-2-(2-{2-[2-(2-methylphenyl)ethyl]phenoxy}ethyl)pyrrolidine [prepared as described in step (a) above] in a suitable amount of ethyl acetate, and the resulting mixture was concentrated by distillation under reduced pressure. The resulting oily residue was dissolved in 7 ml of ethyl acetate, after which it was allowed to stand at room temperature. The crystals which precipitated were collected by filtration, to give 212 mg (yield 54%) of the title compound as colorless crystals, melting at 163°-165° C.

Workup

  1. concentrationthe resulting mixture was concentrated by distillation under reduced pressure
  2. dissolutionThe resulting oily residue was dissolved in 7 ml of ethyl acetate
  3. customto stand at room temperature
  4. customThe crystals which precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8145b4f88b5b43c396752cb3bf413e17
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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