Hydrochloric Acid → 2-(2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}ethyl) piperidine hydrochloride

HRID 743263Notes

Reaction equation

HRID 743263 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][CH2:16][CH2:15][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][NH:9]2)[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 105750741-t-Butoxycarbonyl-2-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidine

Product 1

HCID 194240332-(2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}ethyl) piperidine hydrochlorideYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1 ml of a 4N solution of hydrogen chloride in dioxane was added to a solution of 0.63 g of 1-t-butoxycarbonyl-2-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidine [prepared as described in step (a) above] in 1 ml of dioxane, and the resulting solution was allowed to stand at room temperature for 2.5 hours. At the end of this time, it was concentrated by distillation under reduced pressure. The resulting residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and concentrated by distillation under reduced pressure. The resulting residue was dissolved in ethanol, and the solution was adsorbed on a Column packed with CM Sephadex C-25 (H+ type) (Sephadex is a trade mark). The column was washed with ethanol and eluted with a 0.1N solution of hydrogen chloride in ethanol. The eluate was concentrated by evaporation under reduced pressure and dried in vacuo, to give 0.22 g (yield 40%) of the title compound as a colorless oil.

Workup

  1. concentrationAt the end of this time, it was concentrated by distillation under reduced pressure
  2. customThe resulting residue was partitioned between ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated by distillation under reduced pressure
  5. dissolutionThe resulting residue was dissolved in ethanol
  6. washThe column was washed with ethanol
  7. washeluted with a 0.1N solution of hydrogen chloride in ethanol
  8. concentrationThe eluate was concentrated by evaporation under reduced pressure
  9. customdried in vacuo

Sources & evidence

ORD record
ord-60b1ab8735a84e9d9dc8b900ce7cc0ca
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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