Hydrochloric Acid → (R)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidine hydrochloride

HRID 743323Notes

Reaction equation

HRID 743323 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]2[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=2[O:14][CH2:15][C@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[CH:7]=[CH:8][CH:9]=1.C(O)C>O1CCOCC1>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]2[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=2[O:14][CH2:15][C@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 53979546(R)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidine

Product 1

HCID 57497641(R)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidine hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

0.7 ml of a 4N solution of hydrogen chloride in dioxane was added to a solution of 750 mg of (R)-2-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidine [prepared as described in step (a) above] in a suitable amount of dioxane, and the resulting mixture was concentrated by evaporation under reduced pressure. The resulting oily residue was dissolved in 10 ml of ethyl acetate, and the solution was allowed to stand at room temperature. The crystals which precipitated were collected by filtration and dried in vacuo, to give 686 mg (yield 82%) of the title compound as a colorless powder, melting at 124°-125° C. [α]D25 -4.2° (c=3.45 ethanol).

Workup

  1. concentrationthe resulting mixture was concentrated by evaporation under reduced pressure
  2. dissolutionThe resulting oily residue was dissolved in 10 ml of ethyl acetate
  3. customto stand at room temperature
  4. customThe crystals which precipitated
  5. filtrationwere collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d5067d392113445b8090c715e442eade
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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