Hydrochloric Acid → HCID 68816900, compound

HRID 657125Notes

Reaction equation

HRID 657125 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:29][CH3:30])=[CH:7][C:8](=[O:28])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]2)=[CH:4][CH:3]=1.Cl>O1CCOCC1>[NH2:20][CH:17]1[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=3)[C:6]([O:29][CH3:30])=[CH:7][C:8]2=[O:28])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68816901HCID 68816901, compound

Product 1

HCID 68816900HCID 68816900, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl (1-{2-[7-fluoro-4-(methyloxy)-2-oxo-1(2H)-quinolinyl]ethyl}-4-piperidinyl)carbamate (0.40 g, 0.95 mmol) was stirred in 1,4-dioxane (15 ml) containing 4M HCl for 5 h, then concentrated. The resulting solid was portioned between ethyl acetate and sodium carbonate solution and the aqueous extracted with ethyl acetate. The organics were dried and concentrated to an oil which contained highly impure product. Analysis of the aqueous by 1 c/ms showed the product to primarily reside in the aqueous fraction. The aqueous was concentrated and the resulting solids washed with dichloromethane containing methanol (10%) which on evaporation provided material which was washed once more with dichloromethane containing methanol (10%). Concentration of the solution provided the title compound (0.114 g, 37%).

Workup

  1. concentrationconcentrated
  2. extractionthe aqueous extracted with ethyl acetate
  3. customThe organics were dried
  4. concentrationconcentrated to an oil which
  5. concentrationThe aqueous was concentrated
  6. washthe resulting solids washed with dichloromethane
  7. additioncontaining methanol (10%) which
  8. customon evaporation
  9. customprovided material which
  10. washwas washed once more with dichloromethane
  11. additioncontaining methanol (10%)

Sources & evidence

ORD record
ord-9ca620c42a6744dd93370224c36793ee
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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