Piperidine → HCID 12051145, compound

HRID 428124Notes

Reaction equation

HRID 428124 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.N1CCCCC1.[C:15]([CH2:17][C:18]([NH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][O:31][CH3:32])=[CH:25][CH:24]=1)=[O:19])#[N:16]>C(O)C>[C:15](/[C:17](=[CH:7]\[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)/[C:18]([NH:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][O:31][CH3:32])=[CH:27][CH:28]=1)=[O:19])#[N:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 103713-PyridinecarboxaldehydeHCID 12051144HCID 12051144, compound

Product 1

HCID 12051145HCID 12051145, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Then, ethanol (10 ml), 3-pyridinecarbaldehyde (0.62 g, 5.8 mmol) and a drop of piperidine were added to the resulting 2-cyano-N-(4-methoxymethoxyphenethyl)acetamide (0.96 g, 3,87 mmol) and refluxed under heating for 19 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=19:1) and recrystallized to yield the titled compound (0.83 g, 64%). Properties: mp 105-106° C. (ethyl acetate-hexane)

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 19 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform:methanol=19:1)
  5. customrecrystallized

Sources & evidence

ORD record
ord-f100bfc3cd53426286926281e65c1248
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

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