Water → 4-Benzyl-1-[2-(4-benzyloxy-phenoxy)-ethyl]-piperidin-4-ol

HRID 1419912Notes

Reaction equation

HRID 1419912 reaction equation
[CH2:1]([C:8]1([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(=O)CC>[CH2:1]([C:8]1([OH:14])[CH2:13][CH2:12][N:11]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 981524-Benzyl-4-piperidinolHCID 107570881-(Benzyloxy)-4-(2-bromoethoxy)benzene

Product 1

HCID 700459094-Benzyl-1-[2-(4-benzyloxy-phenoxy)-ethyl]-piperidin-4-olYield 99%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-benzyl-4-hydroxy-piperidine (0.62 g, 3.3 mmol), 1-(2-bromoethoxy)-4-(phenylmethoxy)-benzene (1.0 g, 3.3 mmol) and potassium carbonate (0.9 g, 6.5 mmol) in 2-butanone (15 ml) was refluxed overnight. It was cooled to room temperature, 30 ml of H2O were added and the organic phase was separated. The water phase was extracted two times with ethyl acetate. The organic phases were then pooled, dried with Na2SO4 and the solvent evaporated to give 4-benzyl-1-[2-(4-benzyloxy-phenoxy)-ethyl]-piperidin-4-ol as a yellowish solid (1.35 g, 99%). MS: m/e=418.4 (M+H+).

Workup

  1. temperaturewas refluxed overnight
  2. customthe organic phase was separated
  3. extractionThe water phase was extracted two times with ethyl acetate
  4. dry with materialdried with Na2SO4
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-5c6fbf0f934443f69803fb19aa2206e5
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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