Water → (2-Methylcyclohexyl)Methanamine

HRID 1584581

反応式

HRID 1584581 の反応式
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.O.[H][H].[CH2:13]1[C@@H:21]2[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][NH:14]1>[C].[Ru].C(O)(C)(C)C>[CH2:1]1[C@H:9]2[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][NH:2]1.[CH3:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH:21]1[CH2:13][NH2:14]

参加物

8

反応物 4

HCID 962WaterHCID 422478IsoindolineHCID 10964494cis-OctahydroisoindoleHCID 178418361HCID 178418361、化合物2 回

生成物 2

HCID 21225048(2-Methylcyclohexyl)Methanamine収率 3.8%HCID 36689195(3aR,7aR)-Octahydro-1H-isoindole収率 0.1%

試薬・触媒・溶媒 2

HCID 178503044HCID 178503044、化合物触媒HCID 6386tert-Butanol溶媒

実験手順

In a 3-liter GL autoclave fitted with a electromagnetic stirrer are added 129 g of isoindoline, 516 g of 50% water-containing tert-butyl alcohol and 26 g of 5% ruthenium-carbon catalyst (50% water-containing). The reaction mixture is subjected to a hydrogen-pressure of 30 kg/cm2 and a temperature of 130° C. After a 6 hour hydrogen introduction, the drop in the rate of the hydrogen-absorption is observed, at this point the introduction of hydrogen is ceased to terminate the reaction. After the termination of reaction, the catalyst is filtered out from the reacted solution. By the result of the capillary chromatographic analysis, the yield of cis-hexahydroisoindoline is 96.0%. In addition, 0.1% of trans-hexahydroisoindoline and 3.8% of 2-methylcyclohexylmethylamine is formed. After concentrating the reacted solution, the residue is purified by distillation to give 123.2 g of cis-hexahydroisoindoline (yield 91%).

後処理

  1. customIn a 3-liter GL autoclave fitted with a electromagnetic stirrer
  2. customa temperature of 130° C
  3. customthe drop in the rate of the hydrogen-absorption
  4. customto terminate
  5. customthe reaction
  6. customAfter the termination of reaction
  7. filtrationthe catalyst is filtered out from the reacted solution
  8. customBy the result of the capillary chromatographic analysis

出典と根拠

ORDレコード
ord-0acfcbf59edf442297448657bdbc7e2e
出典データセット
uspto-grants-1999_08
特許番号
US05932744

関連ノート

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