Potassium Hydroxide → 1H-Indol-5-amine, 3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-

HRID 725961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 725961
[OH-].[K+].[NH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>CO.O>[NH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH:16]=1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 788675-Aminoindole

Produkt 1

HCID 111488671H-Indol-5-amine, 3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-Ausbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 1.29 gm (20 mMol) potassium hydroxide in 10 mL methanol were added 1.32 gm (10 mMol) 5-amino-1H-indole followed by 2.46 mL (20 mMol) 1-methyl-4-piperidone. The reaction mixture was then heated to reflux for 18 hours. The reaction mixture was cooled to ambient, diluted with 20 ml water and the precipitate collected by filtration. The solid was recrystallized from ethyl acetate:methanol to give 1.11 gm (48.9%) 5-amino-3-(1-methyl-1,2,3,6-tetrahydropyr-idin-4-yl)-1H-indole as a tan solid (m.p.=200°-203° C.). The tan solid was subjected to flash chromatography, eluting with 100:20:0.5 dichloromethane:methanol:ammonium hydroxide, to give 0.99 gm 5-amino-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole as a cream colored solid (m.p.=212°-215° C. (ethyl acetate:methanol)).

Aufarbeitung

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction mixture was cooled to ambient,
  4. filtrationthe precipitate collected by filtration
  5. customThe solid was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b52587e371504faa819d3272ec2541ab
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05708008

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