Potassium Carbonate → 1-[2-Hydroxy-(2-methoxyphenyloxy)-propyl]-piperidin-4-one

HRID 614362Notes

Reaction equation

HRID 614362 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:18][CH:19]1[O:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[OH:21][CH:19]([CH2:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][CH3:9])[CH2:20][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98357((o-Methoxyphenoxy)methyl)oxiraneHCID 30848514-Piperidone hydrochloride

Product 1

HCID 233473441-[2-Hydroxy-(2-methoxyphenyloxy)-propyl]-piperidin-4-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 20 g of the hydrate of 4-piperidone-hydrochloride, 46.8 g of 1-(2-methoxyphenyloxy)-2,3-epoxy-propane, 18 g of potassium carbonate and 250 ml of isopropanol is stirred for 6 hours at a reaction temperature of 60° C. After cooling, the suspension is filtered and the filtrate is evaporated to dryness under reduced pressure. The residue is dissolved in 100 ml of 6N hydrochloric acid and washed with four 75 ml portions of ethyl acetate. The aqueous acid solution is adjusted with a 2N sodium carbonate solution to a pH of 10 and extracted with three 75 ml portions of ethyl acetate. The organic extracts are dried over sodium sulphate and concentrated under reduced pressure. The red residue is dissolved in methanol and the solution is boiled for 30 minutes with the addition of activated charcoal. The solution is filtered and the filtrate is concentrated under reduced pressure. The residue is treated with toluene and recrystallised from a mixture of ethyl acetate and petroleum ether to give 1-[2-hydroxy-(2-methoxyphenyloxy)-propyl]-piperidin-4-one with a melting point of 77°-78° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe suspension is filtered
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. dissolutionThe residue is dissolved in 100 ml of 6N hydrochloric acid
  5. washwashed with four 75 ml portions of ethyl acetate
  6. extractionextracted with three 75 ml portions of ethyl acetate
  7. dry with materialThe organic extracts are dried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe red residue is dissolved in methanol
  10. additionthe solution is boiled for 30 minutes with the addition of activated charcoal
  11. filtrationThe solution is filtered
  12. concentrationthe filtrate is concentrated under reduced pressure
  13. additionThe residue is treated with toluene
  14. customrecrystallised from a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-114cb3ac6a9342bfbaa3d8ba94b61479
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

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