Citric Acid → 2-(Piperidin-1-yl)benzaldehyde

HRID 730620Notes

Reaction equation

HRID 730620 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7](=O)([O-])[O-].[K+].[K+].O.[C:14](O)(=O)[CH2:15][C:16]([CH2:21][C:22](O)=O)([C:18]([OH:20])=O)O>CN(C=O)C>[N:1]1([C:15]2[CH:14]=[CH:7][CH:22]=[CH:21][C:16]=2[CH:18]=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 8082PiperidineHCID 11430Potassium Carbonate

Product 1

HCID 20621572-(Piperidin-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of the aldehyde 3a (20 g, 161.1 mmol) in dry DMF (160 mL), piperidine (19.1 mL, 193.4 mmol, 1.2 eq) and potassium carbonate (26.73 g, 193.4 mmol, 1.2 eq) were successively added. The suspension was heated at 130° C. for 3 h. The reaction mixture was then poured into cold water and acidified with citric acid up to pH 5. The aqueous layer was extracted 3X with EtOAc and the combined organic extract was successively washed with water, saturated NaHCO3 and brine. After drying the organic extract over MgSO4, filtration and concentration, the desired 2-piperidinobenzaldehyde 3b was isolated as a red oil (28.23 g, 92% yield).

Workup

  1. extractionThe aqueous layer was extracted 3X with EtOAc
  2. extractionthe combined organic extract
  3. washwas successively washed with water, saturated NaHCO3 and brine
  4. customAfter drying the
  5. extractionorganic extract over MgSO4, filtration and concentration

Sources & evidence

ORD record
ord-e0c888889e6c49ef8e4968400b030460
Source dataset
uspto-grants-2009_09
Patent number
US07582766B2

Reaction notes

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