Potassium Carbonate → HCID 118159225, compound

HRID 713193Notes

Reaction equation

HRID 713193 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[F:25][C:26]1[CH:27]=[C:28]([SH:32])[CH:29]=[CH:30][CH:31]=1>C(#N)C>[F:25][C:26]1[CH:27]=[C:28]([S:32][CH:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]2)[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75710m-FluorobenzenethiolHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 118159225HCID 118159225, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of tert-butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate (1.0 g, 3.58 mmol), K2CO3 (0.742 g, 5.37 mmol), and 3-fluorobenzenethiol (0.363 mL, 4.30 mmol) in ACN (7.5 mL) was stirred at 23° C. for 5 min. The reaction mixture was stirred at 80° C. for 17 h, cooled to 23° C. and partitioned between EtOAc and water. The layers were separated, the organic phase was washed with brine, dried over Na2SO4, filtered, rinsed with EtOAc, and dried in vacuo gave tert-butyl 4-((3-fluorophenyl)thio)piperidine-1-carboxylate (1.115 g, 100%) as a yellow oil. ESI-MS m/z [M+H]+ 255.9.

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for 17 h
  2. temperaturecooled to 23° C.
  3. custompartitioned between EtOAc and water
  4. customThe layers were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. washrinsed with EtOAc
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b41632a296dd4b8c938149f6ea0ddd09
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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