Sodium Thiosulfate → HCID 68289948, compound

HRID 68775Notes

Reaction equation

HRID 68775 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 66868496HCID 66868496, compound

Product 1

HCID 68289948HCID 68289948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(5-methyl-pyrazin-2-yl)-piperidin-4-ol (500 mg) and Dess-Martin periodinane (1.30 g) in dichloromethane (20 mL) is stirred at room temperature for 4 h. Aqueous Na2S2O3 solution and NaHCO3 solution are added and the organic phase is separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is triturated with a small amount of methanol. The mixture is filtered and the filtrate is concentrated in vacuo to give the title compound. LC (method 1): tR=0.56 min; Mass spectrum (ESI+): m/z=192 [M+H]+.

Workup

  1. customthe organic phase is separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is triturated with a small amount of methanol
  6. filtrationThe mixture is filtered
  7. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-0d1b2db42649492f85c8194d28b8f569
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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