Methyl 4-[2-fluoro-3-(methylsulfonyl)-phenyl]piperidine-1-carboxylate → 4-[2-Fluoro-3-(methylsulfonyl)phenyl]piperidine

HRID 1879030Notes

Reaction equation

HRID 1879030 reaction equation
[F:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][N:15](C(OC)=O)[CH2:14][CH2:13]1>C(O)C.Cl>[F:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 67532655Methyl 4-[2-fluoro-3-(methylsulfonyl)-phenyl]piperidine-1-carboxylate

Product 1

HCID 574480384-[2-Fluoro-3-(methylsulfonyl)phenyl]piperidineYield 91%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of methyl 4-[2-fluoro-3-(methylsulfonyl)-phenyl]piperidine-1-carboxylate (0.7 g, 2.2 mmol) in ethanol (4 ml), hydrochloric acid (3 M, 10 ml) was added and the mixture was heated at reflux for 24 h. The ethanol was evaporated and the aqueous residue was basified with sodium hydroxide (5 M) and extracted with ethylacetate (3×50 ml). The combined organic phases was washed with brine (50 ml), dried (MgSO4) and evaporated to dryness to give the title compound (0.5 g, 91%). MS m/z (relative intensity, 70 eV) 257 (M+, 6), 237 (95), 208 (83), 173 (bp) 130 (69).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 24 h
  3. customThe ethanol was evaporated
  4. extractionextracted with ethylacetate (3×50 ml)
  5. washThe combined organic phases was washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0e2e4088fae84953a3fc83989aa06616
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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