Piperidine → 1-Aminoanthraquinone

HRID 1731007Notes

Reaction equation

HRID 1731007 reaction equation
N1CCCCC1.[N+:7]([C:10]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:11]=1[C:12](=[O:25])[C:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=1[C:19]2=[O:24])([O-])=O.[H][H]>[Pd].COCCO>[NH2:7][C:10]1[C:11]2[C:12](=[O:25])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19](=[O:24])[C:20]=2[CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 21292556HCID 21292556, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67101-AminoanthraquinoneYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Procedure

1.4 Grams of 5% palladium on carbon catalyst and 52 grams of piperidine were added to a mixture of 154 grams of 5-nitrotetrahydroanthraquinone and 3,000 grams of methyl cellosolve, into which was fed hydrogen at room temperature and under normal pressure for having hydrogen absorbed in the starting 5-nitro compound in an amount of 2 mols per mol of the 5-nitro compound. After completion of the hydrogenation, the catalyst was separated by filtration and air was fed into the resultant filtrate at normal temperature for 1 hour. Then, the resultant solution was concentrated by distilling off the methyl cellosolve until crystals began to precipitate. The thus concentrated solution was allowed to cool and the resultant crystals were separated by filtration, washed with water and dried to obtain 114 grams of 1-aminoanthraquinone having a purity of 98.0%.

Workup

  1. customat room temperature
  2. customabsorbed in the starting 5-nitro compound in an amount of 2 mols per mol of the 5-nitro compound
  3. customAfter completion of the hydrogenation, the catalyst was separated by filtration and air
  4. concentrationThen, the resultant solution was concentrated
  5. distillationby distilling off the methyl cellosolve until crystals
  6. customto precipitate
  7. temperatureto cool
  8. customthe resultant crystals were separated by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-3a06c92a20f94383a2c0d67dcaade20c
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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