Reaktion #68072

ord-a4ce73553b154657bfb00f84b521e7de

Reaktionsgleichung

CN(C)C=O
N,N-dimethylformamide
CCOC(=O)C1(CCCn2c(=O)ccc3ccc(OC)cc32)CCNCC1
ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)C=O
N,N-dimethylformamide
BrCCCc1ccccc1
(3-bromopropyl)benzene
CCOC(=O)C1(CCCn2c(=O)ccc3ccc(OC)cc32)CCN(CCCc2ccccc2)CC1
ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(3-phenylpropyl)piperidine-4-carboxylate

Lösungsmittel

Reaktionsbedingungen

Temperatur
67.5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwere added at room temperature
  2. 2
    workup.ADDITIONwere added
  3. 3
    SonstigeThe organic layer was separated
  4. 4
    Waschenthe mixture was washed sequentially with water and aqueous saturated sodium chloride solution
  5. 5
    Trocknendried over anhydrous magnesium sulfate
  6. 6
    Sonstigethe solvent was removed under reduced pressure

Vorschrift

To 1.25 mL of an N,N-dimethylformamide solution containing 70 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 57 mg of potassium carbonate and 0.25 mL of an N,N-dimethylformamide solution containing 31 μL of (3-bromopropyl)benzene were added at room temperature, and stirred at 60-75° C. for 1.5 hours. After the reaction mixture was cooled to the room temperature, ethyl acetate and water were added. The organic layer was separated, and the mixture was washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 81 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(3-phenylpropyl)piperidine-4-carboxylate as a yellow oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524738B2uspto-grants-2013_09