4-Aminomethylindole

Description

4-Aminomethylindole is a synthetic intermediate useful for pharmaceutical synthesis.

Uses

Reactant for preparation of dopamine receptor antagonists 1 Reactant for preparation of high-affinity ligands to α2δ subunit of voltage-gated calcium channels 2

Uses

4-Aminomethylindole is a useful research intermediate used in the preparation of dopamine receptor antagonist.

Uses

4-(Aminomethyl)indole is used as a reactant for preparation of dopamine receptor antagonists and for preparation of high-affinity ligands to α2δ subunit of voltage-gated calcium channels. It is used as a synthetic intermediate.

Definition

ChEBI: 4-Aminomethylindole is a member of indoles.

Synthesis

The general procedure for the synthesis of 4-(aminomethyl)indole from 4-cyanoindole was as follows:Preparation of C-(1H-indol-4-yl)-methylamine. At room temperature, 4-cyanoindole (7.5 g, 53 mmol) was dissolved in THF (100 ml) and then slowly added to 1.0 M lithium aluminum hydride solution in THF (100 ml). The reaction mixture was heated to reflux for 30 min and subsequently cooled to room temperature. After completion of the reaction, the reaction mixture was quenched with 1N NaOH solution and filtered. The filtrate was acidified with 1N HCl and stirred at room temperature for 10 minutes. Subsequently, the pH was adjusted to about 10, saturated NaHCO3 solution was added and extracted with n-butanol. The organic layer was separated and concentrated to dryness. The residue was ground with methanol, filtered to remove insoluble matter and the filtrate was concentrated under reduced pressure to give the target product. The final product was dried under high vacuum at 50 °C to give a white solid (7.27 g, 94% yield).

References

[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 6, p. 2646 - 2650
[2] Patent: US2012/238569, 2012, A1. Location in patent: Page/Page column 29
[3] European Journal of Medicinal Chemistry, 2017, vol. 134, p. 13 - 23
[4] Catalysis Science and Technology, 2014, vol. 4, # 3, p. 629 - 632