Ammonia → Tricyclo(5.2.1.0,2,6)decan-8-amine

HRID 2416992

Reaction equation

HRID 2416992 reaction equation
[CH:1]12[CH2:11][CH:7]([C:8](=O)[CH2:9]1)[CH:6]1[CH:2]2[CH2:3][CH2:4][CH2:5]1.[NH3:12].[H][H]>CO.[Ni]>[CH2:3]1[CH:2]2[CH:6]([CH:7]3[CH2:11][CH:1]2[CH2:9][CH:8]3[NH2:12])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 965094,7-Methano-5H-inden-5-one, octahydro-HCID 178418361HCID 178418361, compound

Product 1

HCID 86760Tricyclo(5.2.1.0,2,6)decan-8-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 15 g of tricyclo[5,2,1,02,6]decan-8-one in 60 ml of methanol, which had been saturated beforehand at 10° C. with NH3, was, after addition of Raney nickel, hydrogenated in an autoclave at 90° C. and a hydrogen pressure of 100 bar for 10 hours. The catalyst was filtered off and the solvent was distilled off under reduced pressure, and the mixture was then made strongly alkaline using 10 N NaOH and extracted 2-3 times with ethyl acetate or with diisopropyl ether. The combined organic phases were dried and subjected to fractional distillation under reduced pressure. Bp6-7mm 86-88° C.

Workup

  1. customhydrogenated in an autoclave at 90° C.
  2. filtrationThe catalyst was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionextracted 2-3 times with ethyl acetate
  5. customThe combined organic phases were dried
  6. distillationsubjected to fractional distillation under reduced pressure
  7. customBp6-7mm 86-88° C.

Sources & evidence

ORD record
ord-50cf7a5f055241dbbd55c2055c98f7b9
Source dataset
uspto-grants-2004_11
Patent number
US06825231B2

Linked notes

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