Triacetoxyperiodinane → 1-(3-((1-(Quinolin-2-yl)piperidin-4-yl)oxy)pyrazin-2-yl)piperidin-4-one

HRID 454926Notes

Reaction equation

HRID 454926 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[C:19]([N:24]3[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]3)=[N:20][CH:21]=[CH:22][N:23]=2)[CH2:13][CH2:12]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:12][CH2:13][CH:14]([O:17][C:18]2[C:19]([N:24]3[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]3)=[N:20][CH:21]=[CH:22][N:23]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 585478291-(3-((1-(Quinolin-2-YL)piperidin-4-YL)oxy)pyrazin-2-YL)piperidin-4-OL

Product 1

HCID 585478111-(3-((1-(Quinolin-2-yl)piperidin-4-yl)oxy)pyrazin-2-yl)piperidin-4-oneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-((1-(quinolin-2-yl)piperidin-4-yl)oxy)pyrazin-2-yl)piperidin-4-ol (see Example 1.1; 0.10 g, 0.25 mmol) was dissolved in anhydrous CH2Cl2 (10 mL), treated with Dess-Martin periodinane (DMP) (200 mg, 0.50 mmol, 2.0 equiv) and stirred at RT until complete conversion. The organic layer was washed with an aqueous solution of NaHCO3/Na2S2O3 (3×10 mL)), dried over Na2SO4, filtered and evaporated. The resulting residue was purified by flash chromatography on silica gel (20% to 40% EtOAc in petroleum ether) to give 1-(3-((1-(quinolin-2-yl)piperidin-4-yl)oxy)pyrazin-2-yl)piperidin-4-one (0.084 g, 0.20 mmol, 83% yield) as a white solid. ESI-MS (M+1): 404 calc. for C23H25N5O2 403.

Workup

  1. washThe organic layer was washed with an aqueous solution of NaHCO3/Na2S2O3 (3×10 mL)),
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting residue was purified by flash chromatography on silica gel (20% to 40% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-3407825390cf4ecbb065b3b8eb882d4d
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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