Potassium Carbonate → 4-[1-(2-Methyl-8-nitro-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl)-piperidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 604277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604277
F[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:16])[C:7]2=[O:15].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH2:26][N:27]([CH:30]2[CH2:35][CH2:34][N:33]([C:2]3[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]4[C:3]=3[CH2:4][CH2:5][N:6]([CH3:16])[C:7]4=[O:15])[CH2:32][CH2:31]2)[CH2:28][CH2:29]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 17750356tert-Butyl 4-(piperidin-4-yl)piperazine-1-carboxylateHCID 598491765-fluoro-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one

Produkt 1

HCID 598491704-[1-(2-Methyl-8-nitro-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl)-piperidin-4-yl]-piperazine-1-carboxylic acid tert-butyl esterAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 5-fluoro-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one (11.65 g, 0.052 mol), 4-piperidin-4-yl-piperazine-1-carboxylic acid tert-butyl ester (28.0 g, 0.1039 mol), K2CO3 (8.98 g, 0.065 mol) in DMSO (350 mL) was stirred at 85° C. for 12 hours. After cooling to room temperature, ice-water (500 mL) was added. The mixture was extracted with AcOEt. The organic layer was washed with water followed by brine, dried over Na2SO4 and evaporated. The residue was purified by silica gel column chromatography (AcOEt; then AcOEt/MeOH=6/1) to give 10.09 g of the desired product 4-[1-(2-methyl-8-nitro-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl)-piperidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester as pale yellow solid in 41% yield.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with AcOEt
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-ebeaa36887304526a75545382def6811
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910585B2

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