tert-Butyl {1-[2-(7-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate → 1-[2-(4-Amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinolinone

HRID 656860Notes

Reaction equation

HRID 656860 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[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>C(Cl)(Cl)Cl.Cl.CO>[NH2:20][CH:17]1[CH2:18][CH2:19][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)[CH:6]=[CH:7][C:8]2=[O:28])[CH2:15][CH2:16]1

Participants

5

Reactant 1

HCID 86635312tert-Butyl {1-[2-(7-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 667744061-[2-(4-Amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinolinoneYield 64.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

1,1-dimethylethyl {1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-4-piperidinyl}carbamate (1.32 g; 3.39 mmol) was dissolved in a mixture of chloroform (10 ml) and HCl (12 ml) and stirred at rt under argon 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 a neutral pH was reached. This was then filtered and the solvent removed. The crude residue was subjected to chromatography on silica gel using a 0-20% 2M NH3:MeOH/DCM gradient to provide the desired compound (632 mg; 64%)

Workup

  1. customall solvents removed
  2. dissolutionThe residues were redissolved in MeOH
  3. stirringstirred with amberlyst ion exchange resin until a neutral pH
  4. filtrationThis was then filtered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-77b23440b98047eea4b3c55199bc2053
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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