1-Piperidinecarboxaldehyde → HCID 15017674, compound
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
Product 1
Reagents, catalysts & solvents 1
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-for ylpiperidine 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 zO 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
- stirringstirring
- waitcontinued for 2 hours
- additionAn additional 15 g of N-for ylpiperidine was then added every 0.5 hour in 5 g portions
- customThe reaction was quenched with 3N HCl (pH 3) at -78° C
- temperatureThe reaction was warmed to 0° C.
- custompartitioned between zO and ether
- dry with materialThe ether layer was dried
- concentrationconcentrated
- distillationthe residue was distilled
Sources & evidence
- ORD record
- ord-30bb32334b3d463db5e8b4bb9f436a9f
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05256662
Reaction notes
Loading…