HCID 5302983, compound → N1-Tricyclo[3.3.1.13,7]dec-1-yl-1,2-benzenediamine

HRID 2293109Notes

Reaction equation

HRID 2293109 reaction equation
[C:1]12([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:18]([O-])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>C(OCC)(=O)C.[Pt]>[C:1]12([NH:11][C:12]3[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

4

Reactant 1

HCID 5302983HCID 5302983, compound

Product 1

HCID 21476249N1-Tricyclo[3.3.1.13,7]dec-1-yl-1,2-benzenediamineYield 64.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-Adamantan-1-yl-2-nitro-phenylamine (6 g) prepared as in intermediate 10 in ethyl acetate (120 ml) was hydrogenated at 23° and 1 atm. pressure over 5% platinum on carbon (600 mg) for 2 h. The catalyst was removed by filtration through hyflo and the filtrate evaporated to give a brown solid. This was adsorbed onto silica and chromatographed with hexane-EA (20:3) as eluent to give the title compound (3.45 g) as cream crystals, m.p. -69°-71°.

Workup

  1. customwas hydrogenated at 23°
  2. customThe catalyst was removed by filtration through hyflo
  3. customthe filtrate evaporated
  4. customto give a brown solid
  5. customchromatographed with hexane-EA (20:3) as eluent

Sources & evidence

ORD record
ord-44dc4e15debf460eabc2631a7f433927
Source dataset
uspto-grants-1997_11
Patent number
US05686449

Reaction notes

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