Hydrazine → Aminotetrahydrocyclopenta[b]indole

HRID 449822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449822
[CH2:1]1[C:12]2[CH:4]([N:5]=[C:6]3[C:11]=2[CH:10]=[CH:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1.[NH2:13]N.O.NN>>[NH2:13][CH:1]1[C:12]2[CH:4]([N:5]=[C:6]3[C:11]=2[CH:10]=[CH:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 66869719Tetrahydrocyclopent(b)indole

Produkt 1

HCID 66933239Aminotetrahydrocyclopenta[b]indole

Versuchsvorschrift

In Scheme 1, Step C, the phthalimide group of the tetrahydrocyclopenta[b]indole of formula (2) is cleaved with hydrazine or hydrazine hydrate to provide an aminotetrahydrocyclopenta[b]indole of formula (3) using conditions as described by M. Alajarín, et al (Eur. J. Org. Chem. 2002, 4222-4227). The reaction proceeds in a solvent mixture of tetrahydrofuran/ethanol in a ratio of about 5.5/1 by volume at a temperature of 0 to 50° C., preferably at about room temperature, for 4 to 72 hours. The resulting phthalhydrazide is removed by filtration and the product isolated by concentration of the filtrate. It may be purified by chromatography using techniques known in the art.

Quellen und Nachweise

ORD-Eintrag
ord-56fd0fffbc0e42cdb78077eb6db47747
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486943B2

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