Piperidine → 5-(Piperidin-1-yl)-2,3-dihydro-1H-inden-1-one

HRID 2223397Notes

Reaction equation

HRID 2223397 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>N1C=CC=CC=1>[N:12]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 1365375-Fluoro-1-indanone

Product 1

HCID 222283835-(Piperidin-1-yl)-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Fluoroindan-1-one (5 g, 33.3 mmol) and piperidine (8.52 g, 100 mmol, 10 ml) were dissolved in pyridine (20 ml) and heated to reflux for 3 hours. The reaction mixture was cooled, the solvent removed under vacuum, and the residue taken in diethyl ether. The ether solution was washed with 1N aqueous sodium hydroxide and with water, dried with magnesium sulfate, filtered, and the filtrate was removed under vacuum to provide the title compound which was used without further purification. 1H NMR (CDCl3) δ 1.67 (m, 6H), 2.63 (m, 2H), 3.02 (m, 2H), 3.40 (m, 4H), 6.78 (d, 1H), 6.86 (dd, 1H), 7.62 (d, 1H); MS (DCI) 216 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under vacuum
  5. washThe ether solution was washed with 1N aqueous sodium hydroxide and with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate was removed under vacuum

Sources & evidence

ORD record
ord-a697fa1bd4a145949b0ef2a4cbb8067c
Source dataset
uspto-grants-2008_05
Patent number
US07375126B2

Reaction notes

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