Piperidine → HCID 25263859, compound

HRID 563121Notes

Reaction equation

HRID 563121 reaction equation
Br[C:2]1[CH:16]=[C:15]2[C:5]([C:6](=[O:18])[C:7](=[O:17])[C:8]3[S:13][CH2:12][CH:11]([CH3:14])[O:10][C:9]=32)=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:14][CH:11]1[O:10][C:9]2[C:15]3[C:5]([C:6](=[O:18])[C:7](=[O:17])[C:8]=2[S:13][CH2:12]1)=[CH:4][CH:3]=[C:2]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH:16]=3

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 57775486HCID 57775486, compound

Product 1

HCID 25263859HCID 25263859, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 9-bromo-2-methyl-2,3-dihydronaphtho[1,2-b][1,4]oxathiine-5,6-dione (0.1 g, 0.31 mmol) in 1,4-dioxane (1.0 mL) was added piperidine (0.061 mL, 0.616 mmol) and potassium carbonate (0.043 g, 0.308 mmol). The reaction mixture was stirred at 90° C. for 18 hours. The resulting mixture was filtered and solvent was removed under reduced pressure. The crude mixture was purified by flash column chromatography (SiO2, 50% EtOAc in hexanes) to give the product as a purple solid (0.025 g, 25%). M.p.=225-226° C.; 400 MHz 1H NMR (CDCl3) δ: 7.91 (d, J=8.8, 1H), 7.09 (d, J=2.8, 1H), 6.72 (m, 1H), 4.62 (m, 1H), 3.49 (m, 4H), 3.07 (d, J=13.6, 1H), 2.88 (m, 1H), 1.71 (br. s, 6H), 1.60 (d, J=6.4, 3H); LCMS: 330 [M+H].

Workup

  1. filtrationThe resulting mixture was filtered
  2. customsolvent was removed under reduced pressure
  3. customThe crude mixture was purified by flash column chromatography (SiO2, 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6146f209f0ae45258693c6362d3a8261
Source dataset
uspto-grants-2011_11
Patent number
US08067459B2

Reaction notes

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