Hydrochloric Acid → 2-Chloro-6-(4-piperidinyloxy)pyrazine

HRID 1296647Notes

Reaction equation

HRID 1296647 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH:6]=[N:5][CH:4]=1>CO>[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21906088HCID 21906088, compound

Product 1

HCID 181869152-Chloro-6-(4-piperidinyloxy)pyrazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Aqueous 3.0 M HCl (12 mL) was added to a solution of the product obtained in Step 1 above (5.00 g, 15.9 mmol) in methanol (200 mL). The reaction mixture was stirred at 50° C. for 5 h and concentrated in vacuo. The residue was dissolved in water (50 mL) and basified with K3PO4. The aqueous phase was extracted with ethyl acetate (5×40 mL), dried (MgSO4), and concentrated in vacuo. This gave 3.08 g (91%) of the title compound as a colorless oil which slowly decomposed upon standing. HRMS m/z calcd for C9H12ClN3O (M)+ 213.0669, found 213.0663.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (50 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (5×40 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-319d5ba8cc524caaabf6ab86faa93739
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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