Hydrochloric Acid → 1-[2-(4-Amino-1-piperidinyl)ethyl]-5,7-difluoro-2(1H)-quinolinone

HRID 656938Notes

Reaction equation

HRID 656938 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:29])[N:7]2[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]1.Cl>C(Cl)(Cl)Cl.O1CCOCC1.CO>[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:7]2[C:8]3[C:3](=[C:2]([F:1])[CH:11]=[C:10]([F:12])[CH:9]=3)[CH:4]=[CH:5][C:6]2=[O:29])[CH2:20][CH2:19]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86635322tert-Butyl {1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 667740021-[2-(4-Amino-1-piperidinyl)ethyl]-5,7-difluoro-2(1H)-quinolinoneYield 65%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl {1-[2-(5,7-difluoro-2-oxo-1(2H)-quinolinyl)ethyl]-4-piperidinyl}carbamate (2 g; 4.9 mmol) was dissolved in chloroform (20 ml) and 4M HCl in 1,4-dioxane added (20 ml), this was stirred at rt for 1 h. The salts were then dissolved in MeOH and all solvents removed. The residues were redissolved in MeOH and stirred with amberlyst ion exchange resin until neutral pH was reached, the resin was filtered off and solvents removed. The crude residues were purified by column chromatography on silica gel using a 0-20% 2M NH3:MeOH/DCM gradient to give the desired product (970 mg; 65%).

Workup

  1. customall solvents removed
  2. dissolutionThe residues were redissolved in MeOH
  3. stirringstirred with amberlyst ion exchange resin until neutral pH
  4. filtrationthe resin was filtered off
  5. customsolvents removed
  6. customThe crude residues were purified by column chromatography on silica gel using a 0-20% 2M NH3

Sources & evidence

ORD record
ord-7e06e7064f7c489dbb1f20a7907e265b
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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