Piperidine → 3-(Piperidin-1-yl)benzene-1,2-dicarbonitrile

HRID 2100214Notes

Reaction equation

HRID 2100214 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([C:7]#[N:8])[C:5]=1[C:12]#[N:13])([O-])=O.C(=O)([O-])[O-].[K+].[K+].N1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>O>[N:1]1([C:4]2[CH:11]=[CH:10][CH:9]=[C:6]([C:7]#[N:8])[C:5]=2[C:12]#[N:13])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 1626521,2-Benzenedicarbonitrile, 3-nitro-

Product 1

HCID 577971813-(Piperidin-1-yl)benzene-1,2-dicarbonitrileYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-nitrophthalonitrile (497 mg, 2.87 mmol), freshly dried potassium carbonate (2.0 g, 14 mmol) and piperidine (10 mL) was heated at reflux for 4 h. The reaction mixture was poured into water (200 mL) to precipitate the product, which was filtered off and washed with water. The crude product was purified by recrystallisation from aqueous ethanol to give 3 as a beige powder (332 mg, 55%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. customto precipitate the product, which
  4. filtrationwas filtered off
  5. washwashed with water
  6. customThe crude product was purified by recrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-972eab40f3244fb4939b4a3c9f76f1e6
Source dataset
uspto-grants-2009_08
Patent number
US07572327B2

Reaction notes

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