Triethylamine → N-(1-benzylpiperidin-4-yl)-4-amino-2,3,5,6-tetrachloropyridine

HRID 1957520Notes

Reaction equation

HRID 1957520 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:22]([C:25]1[C:30]([Cl:31])=[C:29]([Cl:32])N=[C:27]([Cl:33])[C:26]=1[Cl:34])([O-])=O>O1CCOCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:29]([Cl:32])=[C:30]([Cl:31])[C:25]([NH2:22])=[C:26]([Cl:34])[CH:27]2[Cl:33])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4158521-Benzyl-4-piperidylamineHCID 152291672,3,5,6-Tetrachloro-4-nitropyridine

Product 1

HCID 19068076N-(1-benzylpiperidin-4-yl)-4-amino-2,3,5,6-tetrachloropyridineYield 89.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8.7 g 1-benzyl-4-aminopiperidine, 4.6 g triethylamine and 10 g 4-nitro-2,3,5,6-tetrachloropyridine was added to 100 ml absolute dioxane and stirred for 5 hours at room temperature. After removing dioxane by distillation, the residue was taken up in methylene chloride, admixed with 2 normal hydrochloric acid and stirred vigorously for 30 min. The precipitated precipitate was separated, taken up in a small amount of water, made alkaline with 2 normal ammonia and the aqueous solution was extracted several times with dichloromethane. 13.9 g N-(1-benzylpiperidin-4-yl)-4-amino-2,3,5,6-tetrachloropyridine is obtained as an oil. TLC (mobile solvent: toluene/dioxane/water 9:4.5:0.5), Rf=0.6.

Workup

  1. customAfter removing dioxane
  2. distillationby distillation
  3. stirringstirred vigorously for 30 min
  4. customThe precipitated precipitate was separated
  5. extractionthe aqueous solution was extracted several times with dichloromethane

Sources & evidence

ORD record
ord-2fc2d71eab3f462c8d1b1b873e091c61
Source dataset
uspto-grants-1998_07
Patent number
US05786371

Reaction notes

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