Hydrochloric Acid → 4-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}piperidine hydrochloride

HRID 743249Notes

Reaction equation

HRID 743249 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:31]>O1CCOCC1>[ClH:31].[CH3:30][O:29][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 106215801-t-Butoxycarbonyl-4-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}piperidine

Product 1

HCID 574976154-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}piperidine hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

379 mg of 1-t-butoxycarbonyl-4-{2-[2-(3-methoxyphenyl) ethyl]phenoxy}piperidine [prepared as described in step (a) above] were dissolved in 5 ml of a 4N solution of hydrogen chloride in dioxane, and the solution was allowed to stand at room temperature for 1 hour. The reaction mixture was then concentrated by distillation under reduced pressure, and the resulting oily residue was dissolved in 10 ml of ethyl acetate, after which it was allowed to stand at room temperature. The crystals which precipitated were collected by filtration and dried in vacuo, to give 290 mg (yield 90%) of the title compound as colorless crystals, melting at 121°-122° C.

Workup

  1. concentrationThe reaction mixture was then concentrated by distillation 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-9419fa95fa67405ba805ecde4c7df96d
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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