6-Nitro-2-piperidin-1-ylquinoline → 2-Piperidin-1-ylquinolin-6-amine

HRID 6796

Reaction equation

HRID 6796 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH:8]=[CH:7]2)([O-])=O>CO.[OH-].[OH-].[Pd+2]>[N:14]1([C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[CH:12][CH:13]=[C:4]([NH2:1])[CH:5]=3)[N:10]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

4

Reactant 1

HCID 220189706-Nitro-2-piperidin-1-ylquinoline

Product 1

HCID 220189742-Piperidin-1-ylquinolin-6-amine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The product (204 mg, 0.8 mmol) of Step C and palladium hydroxide on carbon (100 mg) was suspended in methanol. The resulting mixture was degassed then stirred under hydrogen atmosphere (balloon) until all the yellow solids had dissolved. The reaction mixture was filtered through filter aid and the solvent removed under vacuum to afford the product as a brown solid, MS: m/z 228 (MH+), which was used without further purification

Workup

  1. customThe resulting mixture was degassed
  2. dissolutionhad dissolved
  3. filtrationThe reaction mixture was filtered
  4. filtrationthrough filter aid
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-7a8c29af5c6d4ed5850e6a506f148c64
Source dataset
uspto-grants-2006_08
Patent number
US07084156B2

Linked notes

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