Isoquinoline → Decahydroisoquinoline

HRID 542254

Reaction equation

HRID 542254 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1>[C].[Ru]>[CH2:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][NH:2]1

Participants

3

Reactant 1

HCID 8405Isoquinoline

Product 1

HCID 97812DecahydroisoquinolineYield 76%

Reagents, catalysts & solvents 1

HCID 178503044HCID 178503044, compoundCatalyst

Procedure

In an autoclave, 120 g (0.93 mol) of the aforementioned desulfurized isoquinoline 6 g of 5% ruthenium-carbon (Ru/C) catalyst were subjected to hydrogenation at a temperature of 180° C. under a hydrogen pressure of 140 kg/cm2 ·G for 60 hours. The total amount of hydrogen absorbed during the reaction was 4.9 moles and the molar ratio of the absorbed hydrogen to isoquinoline was 5.3. The reaction mixture obtained after separation of the catalyst by filtration was analyzed by gas chromatography. It was found to contain 88% of decahydroisoquinoline. By distilling this reaction mixture, 98 g (76% in yield) of decahydroisoquinoline (197° C. to 210° C. fraction) was obtained. The trans/cis ratio of this decahydroisoquinoline was found to be 6/4.

Workup

  1. customwere subjected to hydrogenation at a temperature of 180° C. under a hydrogen
  2. custom·G for 60 hours
  3. customThe total amount of hydrogen absorbed during the reaction
  4. customThe reaction mixture obtained
  5. customafter separation of the catalyst
  6. filtrationby filtration
  7. distillationBy distilling this reaction mixture

Sources & evidence

ORD record
ord-a712f8464aa642a5a99a1f420a63e56f
Source dataset
uspto-grants-1987_04
Patent number
US04656279

Linked notes

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