Hydrochloric Acid → (4R)-4-Hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine hydrochloride

HRID 743301Notes

Reaction equation

HRID 743301 reaction equation
[ClH:1].[OH:2][C@H:3]1[CH2:7][N:6]([CH3:8])[CH:5]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4]1>O1CCOCC1>[ClH:1].[OH:2][C@H:3]1[CH2:7][N:6]([CH3:8])[CH:5]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54021671(4R)-4-Hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine

Product 1

HCID 67667892(4R)-4-Hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine hydrochlorideYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

0.36 ml of a 4N solution of hydrogen chloride in dioxane was added to a solution of 150 mg of (4R)-4-hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine [prepared as described in step (a) above] in a suitable amount of dioxane, and the resulting mixture was concentrated by distillation under reduced pressure. The resulting solid residue was recrystallized from ethyl acetate, to give 91.6 mg (yield 55%) of the title compound as colorless crystals, melting at 97°-99° C.

Workup

  1. concentrationthe resulting mixture was concentrated by distillation under reduced pressure
  2. customThe resulting solid residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3dfb8e64d26e4cd090efd07cde0a6790
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

Loading…