Hydrochloric Acid → Rimantadine

HRID 1583457

反応式

HRID 1583457 の反応式
[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.Cl>C(O)C.O=[Pt]=O>[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

参加物

5

反応物 2

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

生成物 1

HCID 5071Rimantadine収率 54%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 702Ethanol溶媒

実験手順

1-Adamantyl methyl ketoxime, 2.0 g, was dissolved in 200 ml of ethanol and mixed with 1.0 ml of conc. hydrochloric acid. This solution was poured into a Parr hydrogenation flask, and 1.0 g of PtO2 was added. Hydrogenation under 35 psia (240 KPa) and at room temperature proceeded slowly. After two days of hydrogenation, the catalyst was removed. The filtrate was distilled to dryness and 100 ml water was added to the residue. The insoluble material was removed by filtration and the aqueous layer was basified with sodium hydroxide. The aqueous layer was extracted with ether and the ether layer was separated. The ether layer was then dried over potassium hydroxide pellets and then magnesium sulfate. The resultant ether solution was distilled to remove the solvent providing 1.0 g rimantadine free base (54% yield).

後処理

  1. additionwas added
  2. customat room temperature
  3. customthe catalyst was removed
  4. distillationThe filtrate was distilled to dryness and 100 ml water
  5. additionwas added to the residue
  6. customThe insoluble material was removed by filtration
  7. extractionThe aqueous layer was extracted with ether
  8. customthe ether layer was separated
  9. dry with materialThe ether layer was then dried over potassium hydroxide pellets
  10. distillationThe resultant ether solution was distilled
  11. customto remove the solvent

出典と根拠

ORDレコード
ord-0fa8d051b0f841f0a611983bef9e0083
出典データセット
uspto-grants-1985_11
特許番号
US04551552

関連ノート

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