Hydrochloric Acid → 2-Fluoro-3-(piperidin-3-yl)pyridine dihydrochloride

HRID 473719Notes

Reaction equation

HRID 473719 reaction equation
N#N.[F:3][C:4]1[C:9]([C:10]2[CH2:11][CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH:15]=2)=[CH:8][CH:7]=[CH:6][N:5]=1.[ClH:23].CC(O)C>[Pd].CCO>[ClH:23].[ClH:23].[F:3][C:4]1[C:9]([CH:10]2[CH2:11][CH2:12][CH2:13][NH:14][CH2:15]2)=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 3776IsopropanolHCID 59326930tert-butyl 5-(2-fluoropyridin-3-yl)-3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 674169432-Fluoro-3-(piperidin-3-yl)pyridine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a N2 purged RBF containing tert-butyl 5-(2-fluoropyridin-3-yl)-3,4-dihydropyridine-1(2H)-carboxylate (673 mg, 2.418 mmol) was added 10% Pd/C (50 mg, 0.470 mmol) and EtOH (15 mL). After stirring for 5 minutes, 5N HCl in iPrOH (4.0 mL, 20.00 mmol) was added and the flask capped with a balloon of H2. After 16 hours, LC-MS shows ˜30% conversion. The balloon was refilled. After a further 5 days, LC-MS shows complete consumption of starting material. The reaction was filtered through a celite cartridge and the cartridge rinsed with DCM:10% EtOH (50 mL). The filtrate was concentrated in vacuo to give 2-fluoro-3-(piperidin-3-yl)pyridine dihydrochloride as a yellow foam. The material was carried forward without further purification.

Workup

  1. customthe flask capped with a balloon of H2
  2. waitAfter 16 hours
  3. additionThe balloon was refilled
  4. waitAfter a further 5 days
  5. customconsumption of starting material
  6. filtrationThe reaction was filtered through a celite cartridge
  7. washthe cartridge rinsed with DCM
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-62c035feb20b45138cbc50a5be6a05c7
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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