Indole → 3-(1H-indol-2-yl)propan-1-amine

HRID 250186Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+]>>[NH2:1][CH2:2][CH2:3][CH2:4][C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

Reactant 2

HCID 798Indole

HCID 14798Sodium Hydroxide

Product 1

HCID 223118203-(1H-indol-2-yl)propan-1-amine

Procedure

In step 1 of Scheme B, a 3-amino-propanol compound f is treated with trifluoroacetic anhydride to afford a trifluoroacetylated propyl compound g. In step 2, the trifluoroacetylated compound g, is then heated in the presence of indole h, and the resulting residue treated with base such as sodium hydroxide to provide a 3-aminopropyl indole compound i. Compound i is a compound of formula X in accordance with the invention, wherein R3 is hydrogen.

Sources & evidence

ORD record: ord-3c1e0391ba5549b09e47e6437c45ebd9
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863305B2

Reaction notes

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