4-Pyridinecarboxaldehyde → HCID 68702352, compound

HRID 432782Notes

Reaction equation

HRID 432782 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[N:9]1[CH:14]=[CH:13][C:12](C=O)=[CH:11][CH:10]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[Cl-].[Na+].O>[N:2]1[CH:3]=[CH:4][C:5](=[C:4]2[C:5](=[O:8])[C:6](=[C:12]3[CH:11]=[CH:10][N:9]=[CH:14][CH2:13]3)[CH2:7][N:2]([CH3:1])[CH2:3]2)[CH2:6][CH:7]=1

Participants

6

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 740491-Methyl-4-piperidone

Product 1

HCID 68702352HCID 68702352, compoundYield 182%

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1.0 g (8.84 mmol) of 1-methylpiperidine-4-one and 1.89 g (16.70 mmol) of 4-pyridine carboxaldehyde in 88 mL of a 0.25M solution of aqueous NaOH (22.09 mmol) was added 1.16 mL (0.88 mmol) of a 25% w/w aqueous solution of cetyltrimethylammonium chloride. The mixture was allowed to stir vigorously at room temperature for 3 hours, diluted with 100 ml of brine and extracted with two 60 mL portions of methylene chloride. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo to give 2.15 g (84%) of a yellow-orange powder.

Workup

  1. extractionextracted with two 60 mL portions of methylene chloride
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2179dfe2f8cc4bf293842ce575349435
Source dataset
uspto-grants-2003_12
Patent number
US06664272B2

Reaction notes

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