Potassium Carbonate → HCID 39244817, compound

HRID 1518626Notes

Reaction equation

HRID 1518626 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[O:17]([CH2:16][CH2:15][N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 79341Piperidin-4-ol

Product 1

HCID 39244817HCID 39244817, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4-Hydroxypiperidine (5.06 g, 50 mmol) was dissolved in N,N-dimethylformamide (200 mL), potassium carbonate (13.8 g, 100 mmol) and (2-bromoethoxy)benzene (12.9 g, 60 mmol) were added thereto, and the mixture was stirred at 70° C. for 18 hours. The reaction solution was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain 1-(2-phenoxyethyl)piperidin-4-ol (8.48 g).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-2d5d67bb480c4fef962afd9b4585a3a6
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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