AE-848/34436008 → 3,5-Diamino-N-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide

HRID 1576658Notes

Reaction equation

HRID 1576658 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:7][CH:6]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[C:12]([N+:19]([O-])=O)[CH:11]=2)[CH2:5][C:4]([CH3:24])([CH3:23])[NH:3]1.[H][H]>C(O)C.[Pd]>[NH2:19][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([NH2:16])[CH:13]=1)[C:9]([NH:8][CH:6]1[CH2:5][C:4]([CH3:24])([CH3:23])[NH:3][C:2]([CH3:1])([CH3:25])[CH2:7]1)=[O:22]

Participants

5

Reactant 2

HCID 3139336AE-848/34436008HCID 178418361HCID 178418361, compound

Product 1

HCID 215115913,5-Diamino-N-(2,2,6,6-tetramethylpiperidin-4-yl)benzamideYield 79.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(2,2,6,6-tetramethyl-4-piperidyl)-3,5-dinitrobenzamide (1.0 g.) is dissolved in ethanol (50 ml.) and 10% palladium on charcoal (.1 g.) is added. The reduction is carried out in a Parr apparatus for 2 hours at 40 psi of hydrogen. The catalyst is removed by filtration, washed with a few ml. of ethanol and the filtrate taken to dryness under reduced pressure leaving a tan solid. Recrystallization from ether gives a cream colored product (6.6 g., m.p. 188°-190°C., 79.6% yield).

Workup

  1. customThe catalyst is removed by filtration
  2. washwashed with a few ml
  3. customleaving a tan solid
  4. customRecrystallization from ether
  5. customgives a cream colored product (6.6 g., m.p. 188°-190°C., 79.6% yield)

Sources & evidence

ORD record
ord-e05dd5b829d349baa225c419e1a47753
Source dataset
uspto-grants-1976_09
Patent number
US03982006

Reaction notes

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