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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 565679Generated: October 26, 2026

Trifluoroacetic acid → 1-Phenyl-3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indole

https://huagongshe.com/reaction/565679

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant1-Phenyl-1H-indoleHCID 182029—
ReactantPiperonylamineHCID 2723901—
ReactantAzane;hydrateHCID 12896473—
SolventAcetic AcidHCID 176—
Product1-Phenyl-3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indoleHCID 2211112763%

Reaction Conditions

Temperature120 °C

Reaction Steps

To a heated (110° C.) mixture of 4-piperidone monohydrate hydrochloride (8.2 g), acetic acid (15 mL) and trifluoroacetic acid (30 mL) was added 1-phenyl-1H-indole (3.1 g) under nitrogen atmosphere over a period of 25 min. The mixture was stirred for 30 minutes at 120° C., then cooled and poured into ice. This was neutralized with conc. ammonia water under cooling and the product was extracted thrice with ethyl acetate. The combined extract was washed with water followed by saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was provided for the next reaction without further purification. Yield 63%. Amorphous.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06172085B2
Source datasetuspto-grants-2001_01
ORD IDord-962fd7bdf84944b1a7453bfae665d5d4
Source noteuspto-grants-2001_01