Piperidine → 4-(Piperidine-1-carbonyl)benzaldehyde

HRID 1485104Notes

Reaction equation

HRID 1485104 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.Cl.CN(C)CCCN=C=NCC.O.O[N:26]1[C:30]2C=[CH:32][CH:33]=[CH:34][C:29]=2N=N1.N1CCCCC1.[Cl-].[NH4+]>C(Cl)(Cl)Cl>[N:26]1([C:1]([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)=[O:3])[CH2:32][CH2:33][CH2:34][CH2:29][CH2:30]1

Participants

7

Reactant 5

HCID 8082PiperidineHCID 120884-Formylbenzoic acidHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 190690894-(Piperidine-1-carbonyl)benzaldehydeYield 102.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-carboxybenzaldehyde (1.06 g) in chloroform (14.1 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.03 g), 1-hydroxybenzotriazole monohydrate (1.62 g) and piperdine (1.05 mL) were added. After stirring the mixture at room temperature for 15 hours, a saturated aqueous solution of ammonium chloride was added. After extraction with ethyl acetate, the combined organic layers were washed with saturated brine. The washed organic layers were dried over anhydrous magnesium sulfate and after removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=85:15-30:70) to give the titled compound as a colorless oil (1.57 g).

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washthe combined organic layers were washed with saturated brine
  3. dry with materialThe washed organic layers were dried over anhydrous magnesium sulfate
  4. customafter removing the
  5. filtrationdesiccant by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=85:15-30:70)

Sources & evidence

ORD record
ord-24f40f06325848508d6522151fc4e203
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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