1-Isopropylpiperazine → 2-{3-[4-(1-Methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline
Reaktionsgleichung
[C:1]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:17]([O-:19])=[O:18])=[C:10]([O:15][CH3:16])[CH:11]=2)[CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[CH:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([CH3:22])[CH3:21]>CO>[CH3:21][CH:20]([N:23]1[CH2:28][CH2:27][N:26]([CH2:3][CH2:2][C:1]([N:5]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][C:9]([N+:17]([O-:19])=[O:18])=[C:10]([O:15][CH3:16])[CH:11]=3)[CH2:6]2)=[O:4])[CH2:25][CH2:24]1)[CH3:22]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
A solution of 2-acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (425 mg, 1.62 mmol) in methanol (5 mL) was treated with 1-isopropylpiperzine (1.0 mL, 7.0 mmol, Oakwood Products) and heated at 65° C. in a sealed tube for 16 h. The mixture was cooled, concentrated, and partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic layer was separated, dried over magnesium sulfate, filtered, and purified by chromatography on SiO2 (dichloromethane to 25% methanol/dichloromethane) to give 2-{3-[4-(1-methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (285 mg, 0.731 mmol, 45%). ESIMS (M+H)+=391.
Aufarbeitung
- temperatureThe mixture was cooled
- concentrationconcentrated
- custompartitioned between ethyl acetate and saturated aqueous ammonium chloride
- customThe organic layer was separated
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- custompurified by chromatography on SiO2 (dichloromethane to 25% methanol/dichloromethane)
Quellen und Nachweise
- ORD-Eintrag
- ord-5d23273814da4404bac5057f7c93d49e
- Quelldatensatz
- uspto-grants-2011_07
- Patentnummer
- US07981903B2
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