Piperidine → HCID 53788046, compound

HRID 726672Notes

Reaction equation

HRID 726672 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C:15]#[N:16])[CH:9]=1.N1CCCCC1>CO>[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[CH:6][C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)[C:15]#[N:16])[CH:9]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 13854Pyrrole-2-carboxaldehydeHCID 809233-Pyridineacetonitrile

Product 1

HCID 53788046HCID 53788046, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of pyrrole-2-carboxaldehyde (2.85 g; 30 mmol), 3-pyridylacetonitrile (3.54 g; 30 mmol), and piperidine (2 mL) in methanol (50 mL) was refluxed for 18 hours. The dark precipitate formed was separated by filtration. Dark solid was treated with charcoal in hot methanol to obtain 2.8 g (48%) of the title compound as a yellow solid, m.p. 139°-142° C. Anal. Calcd. for C12H9N3 : C, 73.83; H, 4.65; N, 21.52. Found: C, 73.71; H, 4.57; N, 21.76. Mass spectrum: (EI; M+) m/z 195. 1H-NMR (DMSO-d6 ; 200 MHz) δ 11.5 (s, 1H), 8.8 (d, 1H), 8.5 (d, 1H), 7.92-7.96 (m, 1H), 7.8 (s, 1H), 7.43-7.52 (m, 1H), 7.2 (d, 2H), 6.38-6.4 ppm (q, 1H).

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe dark precipitate formed
  3. customwas separated by filtration
  4. additionDark solid was treated with charcoal in hot methanol

Sources & evidence

ORD record
ord-0f4fe87f08d64bbbbbbb2e6d3fc9c26d
Source dataset
uspto-grants-1998_01
Patent number
US05710164

Reaction notes

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