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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 49508Generated: October 29, 2026

Trifluoroacetic acid → Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine

https://huagongshe.com/reaction/49508

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl esterHCID 69514122—
SolventDichloromethaneHCID 6344—
ProductAllyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amineHCID 2196663894%

Reaction Steps

2.45 g (6.8 mmol) 5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 5 ml CH2Cl2 were treated with 4 ml TFA at 0° C. The solution was stirred at RT for 0.5 h, and at 40° C. for 1 h. The solution was concentrated and the residue was dissolved in ether and water. 2M NaOH was added and the inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4 to yield 1.65 g (94%) Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine as light yellow oil, MS: 259 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06706751B2
Source datasetuspto-grants-2004_03
ORD IDord-5349ffd3e87844e78c7075901f7151a7
Source noteuspto-grants-2004_03