1-Piperidinecarboxaldehyde → HCID 15017674, compound

HRID 1196839Notes

Reaction equation

HRID 1196839 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[F:10].[Li+].CC([N-]C(C)C)C.[CH:19](N1CCCCC1)=[O:20]>C1COCC1>[Br:1][C:2]1[C:3]([F:10])=[C:4]([C:5]([F:9])=[C:6]([F:8])[CH:7]=1)[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 174291-Piperidinecarboxaldehyde2×HCID 675971-Bromo-2,4,5-trifluorobenzeneHCID 2724682Lithium diisopropylamide

Product 1

HCID 15017674HCID 15017674, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-bromo-2,4,5-trifluoro benzene (25 g, 0.12 mol) in THF (200 mL at -78° C. was added LDA (80 mL, 1.5 M) dropwise. The mixture was stirred at -78° C. for 1 hour, then N-formylpiperidine (16 g, 0.144 mol) was added in one portion and stirring continued for 2 hours. An additional 15 g of N-formylpiperidine was then added every 0.5 hour in 5 g portions. The reaction was quenched with 3N HCl (pH 3) at -78° C. The reaction was warmed to 0° C. and partitioned between H2O and ether. The ether layer was dried and concentrated and the residue was distilled to provide 13 g (45%) of the desired aldehyde; bp 63°-65° C. (0.2 mm).

Workup

  1. stirringstirring
  2. waitcontinued for 2 hours
  3. customThe reaction was quenched with 3N HCl (pH 3) at -78° C
  4. temperatureThe reaction was warmed to 0° C.
  5. custompartitioned between H2O and ether
  6. dry with materialThe ether layer was dried
  7. concentrationconcentrated
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-84f19543d27e4a6f986004fbe8991e49
Source dataset
uspto-grants-1992_05
Patent number
US05116834

Reaction notes

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