1-Piperidinecarboxaldehyde → HCID 71743951, compound

HRID 624310Notes

Reaction equation

HRID 624310 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7](I)[C:6]=2[C:18]=1[F:19].C([Li])CCC.N1([CH:31]=[O:32])CCCCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([CH:31]=[O:32])[C:6]=2[C:18]=1[F:19]

Participants

5

Reactant 3

HCID 174291-PiperidinecarboxaldehydeHCID 71743950HCID 71743950, compoundHCID 178418339Butyllithium

Product 1

HCID 71743951HCID 71743951, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
78 °C

Procedure

To a mixture of 5-chloro-4-fluoro-2-(4-fluorophenyl)-3-iodobenzofuran (2.0 g, 5.12 mmol) in THF (15 ml) under a N2 atmosphere in a 50 ml two necked RB flask cooled to 78° C. was added n-butyllithium (0.328 g, 5.12 mmol) slowly, and the mixture stirred at the same temperature for 1 hour. 1-Piperidinecarboxaldehyde (5.79 g, 51.2 mmol) was then added and the mixture was maintained stirring at the same temperature for 3 hours. The reaction mixture was quenched with 1N HCl and extracted with diethyl ether (3×25 ml). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give the titled compound (1.2 g, 74%). 1H NMR (400 MHz, CDCl3): δ 10.39 (d, J=2.4 Hz, 1H), 8.18-8.14 (m, 2H), 7.44-7.40 (m, 1H), 7.33 (d, J=9.2, 1H), 7.27-7.23 (m, 2H).

Workup

  1. temperaturethe mixture was maintained
  2. stirringstirring at the same temperature for 3 hours
  3. customThe reaction mixture was quenched with 1N HCl
  4. extractionextracted with diethyl ether (3×25 ml)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-16546fb097ce4ca1a66225301f8242f7
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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