Sodium Sulfate → 1-C-Ethylaminoadamantane

HRID 461995

反応式

HRID 461995 の反応式
[C:1]12([CH2:11][C:12]([NH2:14])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:1]12([CH2:11][CH2:12][NH2:14])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

参加物

5

反応物 3

HCID 24436Sodium SulfateHCID 86819Tricyclo(3.3.1.13,7)decan-1-acetamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 642451-C-Ethylaminoadamantane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

In this preparation a mixture containing 15 g. of 1-adamantyl acetic acid and 40 ml. of thionyl chloride is allowed to stand for 16 hours at room temperature. The excess thionyl chloride is then removed by evaporation, under reduced pressure, at 60° C affording adamant-1-yl acetyl chloride as an oil. The oil is then dissolved in 800 ml. of ethyl ether and then ammonia is bubbled through the solution until about 12.8 g. is absorbed. The solution is then washed twice with water, dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated under vacuum affording adamant-1-yl acetamide. 12.8 G. of adamant-1-yl acetamide is added to a mixture containing 3 g. of lithium aluminum hydride in 500 ml. of anhydrous tetrahydrofuran at 25°0 C and refluxed for 5 minutes. The mixture is cooled to 5° C, a slight excess of an aqueous saturated solution of sodium sulfate is added dropwise. Thereafter the tetrahydrofuran solution is dried over sodium sulfate, filtered and the solvent evaporated to dryness under vacuum. From the remaining oil, 2-(adamant-1-yl)ethylamine is distilled bulb to bulb, 10.1 g.

後処理

  1. additioncontaining 3 g
  2. dry with materialThereafter the tetrahydrofuran solution is dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated to dryness under vacuum
  5. distillationFrom the remaining oil, 2-(adamant-1-yl)ethylamine is distilled bulb to bulb, 10.1 g

出典と根拠

ORDレコード
ord-fb60f532233b4834a9bc65dd27633b12
出典データセット
uspto-grants-1977_12
特許番号
US04064258

関連ノート

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