Hydrochloric Acid → Rimantadine Hydrochloride

HRID 1583455

반응식

HRID 1583455 반응식
[CH3:1][C:2]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)=[N:3]O.[ClH:15]>[Pt].C(O)C>[CH3:1][CH:2]([NH2:3])[C:5]12[CH2:6][CH:7]3[CH2:13][CH:11]([CH2:10][CH:9]([CH2:8]3)[CH2:14]1)[CH2:12]2.[ClH:15]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 28022691-Adamantan-1-yl-ethanone oxime

생성물 1

HCID 15165Rimantadine Hydrochloride수율 75%

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 702Ethanol용매

실험 절차

Into a Parr hydrogenation flask were placed 0.35 g of 5% Pt/C, 1.9 g of 1-adamantyl methyl ketoxime, 230 ml of ethanol and 2.0 ml of conc. hydrochloric acid. The flask was purged with hydrogen and then the hydrogenation reaction was initiated. Pressure was set at 34 psia (234 KPa) at ambient temperature and the reaction conducted overnight. The catalyst was removed by filtration and washed with 50 ml ethanol. The combined ethanol solution was distilled to dryness under vacuum. The remaining white solid was dissolved in 70 ml of water, and extracted twice with 50 ml ether. The ether layer was discarded. The aqueous layer was basified to pH 10-13 with sodium hydroxide and extracted twice with 100 ml of ether. The ether layer was dried over potassium hydroxide and magnesium sulfate which was removed by filtration. The dried ether layer was treated with hydrogen chloride gas and rimantadine hydrochloride precipitated. The solid was collected by filtration and dried to give 1.6 g of rimantadine hydrochloride (75% yield).

후처리

  1. customThe flask was purged with hydrogen
  2. customthe hydrogenation reaction
  3. customwas set at 34 psia (234 KPa) at ambient temperature
  4. customThe catalyst was removed by filtration
  5. washwashed with 50 ml ethanol
  6. distillationThe combined ethanol solution was distilled to dryness under vacuum
  7. dissolutionThe remaining white solid was dissolved in 70 ml of water
  8. extractionextracted twice with 50 ml ether
  9. extractionextracted twice with 100 ml of ether
  10. dry with materialThe ether layer was dried over potassium hydroxide and magnesium sulfate which
  11. customwas removed by filtration
  12. additionThe dried ether layer was treated with hydrogen chloride gas and rimantadine hydrochloride
  13. customprecipitated
  14. filtrationThe solid was collected by filtration
  15. customdried

출처 및 근거

ORD 기록
ord-772f9c2c35ec4b3191a982e130317835
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04551552

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