Hydrochloric Acid → (2-Methylcyclohexyl)Methanamine

HRID 1584582Notes

Reaction equation

HRID 1584582 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)C1C=CC=CC=1.Cl.[H][H].[CH2:20]1[C@@H:28]2[C@@H:23]([CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:22][NH:21]1>[C].[Pd]>[CH2:9]1[C@H:10]2[C@@H:15]([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:16][NH:8]1.[CH3:22][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH:28]1[CH2:20][NH2:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14027062-Benzyl-2,3-dihydro-1H-isoindoleHCID 10964494cis-OctahydroisoindoleHCID 178418361HCID 178418361, compound2×

Product 2

HCID 21225048(2-Methylcyclohexyl)MethanamineYield 0.7%HCID 36689195(3aR,7aR)-Octahydro-1H-isoindoleYield 0.1%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

In a 3-liter GL autoclave fitted with a electromagnetic stirrer are added 226.5 g of N-benzylisoindoline, 545 g of 7.2% hydrochloric acid aqueous solution (pH 4.0) and 26 g of 5% palladium-carbon catalyst (50% water-containing). The reaction mixture is subjected to a hydrogen-pressure of 20 kg/cm2 and a temperature of 130° C. After a 10 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 83.8%. In addition, 0.1% of trans-hexahydroisoindoline and 0.7% of 2-methylcyclohexylmethylamine is formed. After cooling the reacted solution, 240 g of 20% sodium hydroxide aqueous solution is added to neutralize, and it is extracted with toluene. After concentrating the organic phase, the residue is purified by distillation to give 99.7 g of cis-hexahydroisoindoline (yield 79.6%).

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-54f55c07b69d4b13b178336dca3f8097
Source dataset
uspto-grants-1999_08
Patent number
US05932744

Reaction notes

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