Toluene → 1-[2-(4-aminopiperidin-1-yl)ethyl]-7-methoxyquinolin-2(1H)-one

HRID 656883

Reaktionsgleichung

Reaktionsgleichung von HRID 656883
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:29])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[CH:5][CH:4]=1.C1(C)C=CC=CC=1>C(Cl)(Cl)Cl.Cl.CO>[NH2:21][CH:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:29])[CH2:16][CH2:17]1

Komponenten

6

Edukt 2

HCID 1140TolueneHCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Produkt 1

HCID 593982891-[2-(4-aminopiperidin-1-yl)ethyl]-7-methoxyquinolin-2(1H)-oneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl (1-{2-[7-(methyloxy)-2-oxo-1(2H)-quinolinyl]ethyl}-4-piperidinyl)carbamate (2.25 g; 5.61 mmol) was dissolved in a mixture of chloroform (20 ml) and HCl (15 ml) and stirred at rt under argon for 1 hour. The salts were dissolved in MeOH and a small amount of toluene added, all the solvents were then removed. The residues were redissolved in MeOH and stirred with amberlyst ion exchange resin until a neutral pH was reached. The resin was filtered off and the solvent removed and 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 (900 mg; 54%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-38651200edb34560991f3e690c603ce7
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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