4-(Aminomethyl)piperidine → 4-(2,3,5,6-Tetrachloropyridin-4-ylaminomethyl)pyridine

HRID 1957522Notes

Reaction equation

HRID 1957522 reaction equation
[N+:1]([C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[N:7]=[C:6]([Cl:12])[C:5]=1[Cl:13])([O-])=O.N[CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>O1CCOCC1>[Cl:11][C:8]1[C:9]([Cl:10])=[C:4]([NH:1][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:5]([Cl:13])=[C:6]([Cl:12])[N:7]=1

Participants

4

Reactant 2

HCID 235274-(Aminomethyl)piperidineHCID 152291672,3,5,6-Tetrachloro-4-nitropyridine

Product 1

HCID 190680884-(2,3,5,6-Tetrachloropyridin-4-ylaminomethyl)pyridineYield 24.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1 g 4-nitro-2,3,5,6-tetrachloropyridine, 0.65 g 4-aminomethylpiperidine and 20 ml absolute dioxane were stirred for 1 hour at room temperature. Subsequently the dioxane was removed by distillation, the residue was admixed with water, separated from undissolved material and the aqueous phase was extracted several times with dichloromethane. After drying and evaporating the solvent, the residue can be crystallized from a small amount of diethyl ether. 0.3 g 4-(2,3,5,6-tetrachloropyridin-4-ylaminomethyl)pyridine is obtained as colourless crystals. TLC (mobile solvent: toluene/dioxane/water 90:20:0.2), Rf=0.8.

Workup

  1. customSubsequently the dioxane was removed by distillation
  2. customseparated from undissolved material
  3. extractionthe aqueous phase was extracted several times with dichloromethane
  4. customAfter drying
  5. customevaporating the solvent
  6. customthe residue can be crystallized from a small amount of diethyl ether

Sources & evidence

ORD record
ord-84fabf165bc542ec84c65cb7c38a9b47
Source dataset
uspto-grants-1998_07
Patent number
US05786371

Reaction notes

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