1-Adamantan-1-yl-ethanone oxime → Rimantadine

HRID 1583456

反応式

HRID 1583456 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>[Pt].C(O)(=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

参加物

4

反応物 1

HCID 28022691-Adamantan-1-yl-ethanone oxime

生成物 1

HCID 5071Rimantadine収率 96%

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 176Acetic Acid溶媒

実験手順

Into a Parr hydrogenation flask were placed 8.0 g of 1-adamantyl methyl ketoxime, 200 ml of glacial acetic acid, and 2.8 g of 5% Pt/C. Hydrogenation was continued overnight at 39 psia (270 KPa) and at ambient temperature. The catalyst was removed by filtration and the acetic acid solution was concentrated to one-third of the original volume by vacuum distillation. Water, 200 ml, was added to this conc. acetic acid solution and it was made basic with sodium hydroxide to give a milky solution. The milky solution was extracted three times with 100 ml of methylene chloride. The combined methylene chloride layer was dried over magnesium sulfate which was removed by filtration. The methylene chloride solution was distilled under vacuum to give 7.1 g of clear liquid rimantadine free base (96% yield).

後処理

  1. customThe catalyst was removed by filtration
  2. concentrationthe acetic acid solution was concentrated to one-third of the original volume by vacuum distillation
  3. additionWater, 200 ml, was added to this conc. acetic acid solution and it
  4. customto give a milky solution
  5. extractionThe milky solution was extracted three times with 100 ml of methylene chloride
  6. dry with materialThe combined methylene chloride layer was dried over magnesium sulfate which
  7. customwas removed by filtration
  8. distillationThe methylene chloride solution was distilled under vacuum

出典と根拠

ORDレコード
ord-a9d5bc16315e41e68865ec9e0421dc66
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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