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

HRID 1855985
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HRID 1855985 반응식
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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
60 °C

실험 절차

The starting material can be prepared as follows: 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 6 N hydrochloric acid and washed with four 75 ml portions of ethyl acetate. The aqueous acid solution is adjusted with a 2 N 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.

후처리

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

출처 및 근거

ORD 기록
ord-6610b028b58b4e458f42014686c0537d
출처 데이터셋
uspto-grants-1980_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04217350

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