HCID 12720760, compound → HCID 54256089, compound

HRID 1773498Notes

Reaction equation

HRID 1773498 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)([O-])=O>[Pd].C(O)C>[N:13]1([C:5]2[C:6]([NH2:10])=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 1

HCID 12720760HCID 12720760, compound

Product 1

HCID 54256089HCID 54256089, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(2,6-dinitro-phenyl)-piperidine (2.31 g) and palladium on carbon (10%, 230 mg) in ethanol (80 mL) was stirred under hydrogen atmosphere (1 atm.), at room temperature, for 40 hours. The catalyst was filtered off on a CELITE™ pad. The filtrate was evaporated under reduced pressure and the residue was purified by flash chromatography (hexane/EtOAc, 80/20) to afford 1.29 g of 2-piperidin-1-yl-benzene-1,3-diamine as an orange solid without further purifications.

Workup

  1. filtrationThe catalyst was filtered off on a CELITE™ pad
  2. customThe filtrate was evaporated under reduced pressure
  3. customthe residue was purified by flash chromatography (hexane/EtOAc, 80/20)

Sources & evidence

ORD record
ord-def4d533c8e44d3ab4e005f16ee52889
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

Loading…