Piperidine → HCID 67187268, compound

HRID 451616Notes

Reaction equation

HRID 451616 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[CH2:6][CH2:5]2.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>N1C=CC=CC=1>[F:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:12])=[CH:3][C:2]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 117689445,6-Difluoro-1-indanone

Product 1

HCID 67187268HCID 67187268, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5,6-difluoro-indan-1-one (2.49 g, 14.8 mmol) and piperidine (4.4 ml, 3.78 g, 44.4 mmol) were dissolved in pyridine (10 ml) and heated to reflux for 16 hours. The reaction was cooled, and the solvent removed under vacuum. The residue was taken in ethyl ether, washed with 1N aqueous sodium hydroxide and water, dried with magnesium sulfate, and the solvent removed under vacuum to give the desired product as 2.97 g of a black solid that was used without further purification. 1H NMR (300 MHz, CDCl3) 7.32 (d, 1H), 6.88 (d, 1H), 3.19 (m, 4H), 3.03 (m, 2H), 2.66 (m, 2H), 1.73 (m, 4H), 1.62 (m, 2H). MS (CSI) m/e 234 (M+H)+

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction was cooled
  4. customthe solvent removed under vacuum
  5. washwashed with 1N aqueous sodium hydroxide and water
  6. dry with materialdried with magnesium sulfate
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-b394b8a175d84154a5a9758629da0424
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Reaction notes

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