Hydrochloric Acid → 4-Fluoro-4-phenylpiperidine

HRID 1429223Notes

Reaction equation

HRID 1429223 reaction equation
Cl.[F:2][C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1>O1CCOCC1>[F:2][C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59050060Tert-butyl 4-fluoro-4-phenylpiperidine-1-carboxylate

Product 1

HCID 459337604-Fluoro-4-phenylpiperidineYield 104.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrochloric acid (4 M in dioxane, 20 mL, 80 mmol) was added to a solution of tert-butyl 4-fluoro-4-phenylpiperidine-1-carboxylate (8.27 g, 29.6 mmol) in dioxane (10 mL). The reaction was stirred at ambient temperature for 4 hours. The reaction was concentrated to an oil. Ether was added, and the resulting solid was sonicated and then stirred vigorously overnight to provide a tan solid. The solid was filtered, rinsed with ether and dried under vacuum at 60° C. for 3 hours to provide 5.56 g (87%) of the titled product. MS (DCI) m/z 180 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated to an oil
  2. additionEther was added
  3. customthe resulting solid was sonicated
  4. stirringstirred vigorously overnight
  5. customto provide a tan solid
  6. filtrationThe solid was filtered
  7. washrinsed with ether
  8. customdried under vacuum at 60° C. for 3 hours

Sources & evidence

ORD record
ord-5511477c10f1405698c97ed511fcaebd
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

Loading…