Triethylamine → 5-(piperazin-1-yl)-1H-indole

HRID 225432Notes

Reaction equation

HRID 225432 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Cl.Cl[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]Cl.C(N(CC)CC)C>C(O)CCC>[N:1]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 788675-AminoindoleHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 221748205-(piperazin-1-yl)-1H-indoleYield 100%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-aminoindole (6.23 g, 47 mmol), bis(2-chloroethyl)amine hydrochloride (16.8 g, 96 mmol) and triethylamine (19 mL, 141 mmol) in butanol is heated at 100° C. for 8 hours, cooled to room temperature and concentrated in vacuo to give 9.46 g of 5-piperazin-1-yl-1H-indole.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6d51b368a854fdcbe7745b492ae155c
Source dataset
uspto-grants-2009_07
Patent number
US07557098B2

Reaction notes

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