Piperidine → HCID 86637633, compound

HRID 2384570Notes

Reaction equation

HRID 2384570 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=O)=[CH:4][CH:3]=1.[C:14]([C:16]([C:25]#[N:26])=[C:17]1[CH:22]=[C:21]([CH3:23])[O:20][C:19]([CH3:24])=[CH:18]1)#[N:15].N1CCCCC1>C(O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](/[CH:12]=[CH:23]/[C:21]2[O:20][C:19]([CH3:24])=[CH:18][C:17](=[C:16]([C:25]#[N:26])[C:14]#[N:15])[CH:22]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1199154-(Dicyanomethylene)-2,6-dimethyl-4H-pyranHCID 3442904-Hydroxy-1-naphthaldehyde

Product 1

HCID 86637633HCID 86637633, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-hydroxy-1-naphtaldehyde (0.70 g (5.81 mmol)), 4-(dicyanomethylene)-2,6-dimethyl-4H-pyrane (1.0 g (5.81 mmol)), piperidine (0.50 g (5.81 mmol)), and ethanol (50 mL) were added to a 50-mL three-neck flask. The resultant was heated and refluxed under an argon atmosphere for 6 hours and then the solvent was removed under reduced pressure, followed by purification by column chromatography (SiO2, CHCl3:MeOH=10:1 (v/v)). Thus a desired compound was obtained (yield: 48.2%).

Workup

  1. temperatureThe resultant was heated
  2. temperaturerefluxed under an argon atmosphere for 6 hours
  3. customthe solvent was removed under reduced pressure
  4. customfollowed by purification by column chromatography (SiO2, CHCl3:MeOH=10:1 (v/v))

Sources & evidence

ORD record
ord-e507d3be30af438188edc2457d9b44c0
Source dataset
uspto-grants-2012_09
Patent number
US08263791B2

Reaction notes

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