Water → (2-Methylcyclohexyl)Methanamine

HRID 1584581Notes

Reaction equation

HRID 1584581 reaction equation
[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]

Participants

8

Reactant 4

HCID 962WaterHCID 422478IsoindolineHCID 10964494cis-OctahydroisoindoleHCID 178418361HCID 178418361, compound2×

Product 2

HCID 21225048(2-Methylcyclohexyl)MethanamineYield 3.8%HCID 36689195(3aR,7aR)-Octahydro-1H-isoindoleYield 0.1%

Reagents, catalysts & solvents 2

HCID 178503044HCID 178503044, compoundCatalystHCID 6386tert-ButanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-0acfcbf59edf442297448657bdbc7e2e
Source dataset
uspto-grants-1999_08
Patent number
US05932744

Reaction notes

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