HCID 15869635, compound → HCID 86754368, compound

HRID 1584583Notes

Reaction equation

HRID 1584583 reaction equation
[CH2:1]([N:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[H][H].C(N1C[C@H]2[C@H](CCCC2)C1)CCCCCCCC>[C].[Rh].CC(O)C>[CH2:1]([N:10]1[CH2:11][C@H:12]2[C@@H:17]([CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 15869635HCID 15869635, compoundHCID 54358023HCID 54358023, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86754368HCID 86754368, compoundYield 0.5%

Reagents, catalysts & solvents 2

HCID 178503043HCID 178503043, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

In a 3-liter GL autoclave fitted with a electromagnetic stirrer are added 265 g of N-nonylisoindoline, 735 g of 2-propanol and 26 g of 5% rhodium-carbon catalyst (50% water-containing). The reaction mixture is subjected to a hydrogen-pressure of 15 kg/cm2 and a temperature of 120° C. After a 5 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-hexahydro-N-nonylisoindoline is 98.0%. In addition, 0.5% of trans-hexahydro-N-nonylisoindoline is formed.

Workup

  1. customIn a 3-liter GL autoclave fitted with a electromagnetic stirrer
  2. customa temperature of 120° 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-a7762b670e5c4ed492a26e8d4aa1ee8e
Source dataset
uspto-grants-1999_08
Patent number
US05932744

Reaction notes

Loading…