Aluminium lithium hydride → 2,8-dimethyl-5-(2-(4-methylpiperazin-1-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 574546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574546
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[CH2:31][CH2:30][C:11]2[N:12]([CH2:20][C:21]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=O)[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1>C1COCC1>[CH3:7][N:8]1[CH2:31][CH2:30][C:11]2[N:12]([CH2:20][CH2:21][N:23]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]3)[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 578763372-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(4-methylpiperazin-1-yl)ethanone

Produkt 1

HCID 578762952,8-dimethyl-5-(2-(4-methylpiperazin-1-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleAusbeute 22,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

LAH (0.022 g, 0.58 mmol) was charged in dry THF (3 mL) and cooled to 0 deg C., 2-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(4-methylpiperazin-1-yl)ethanone (0.05 g, 0.147 mmol) was added to it portion wise. The reaction mixture was refluxed for 4 h. The reaction mixture was cooled to 0 deg C. and quenched with sat. Na2SO4. The solid formed was filtered through celite, washed with THF, dried over Na2SO4 and concentrated under reduced pressure to obtain 11 mg of 2,8-dimethyl-5-(2-(4-methylpiperazin-1-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as TFA salt after purification by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).

Aufarbeitung

  1. temperaturecooled to 0 deg C
  2. temperatureThe reaction mixture was refluxed for 4 h
  3. temperatureThe reaction mixture was cooled to 0 deg C
  4. customand quenched with sat. Na2SO4
  5. customThe solid formed
  6. filtrationwas filtered through celite
  7. washwashed with THF
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3903d86a08114265a6d3910b8f929c7c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034880B2

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