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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1929207Generated: October 31, 2026

Diisopropylethylamine → 4-(4-Methoxy-phenyl)-1H-indole-2-carboxylic acid (1-benzyl-piperidin-4-yl)-amide

https://huagongshe.com/reaction/1929207

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant1-Benzyl-4-piperidylamineHCID 415852—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant4-(4-Methoxy-phenyl)-1H-indole-2-carboxylic acidHCID 66841346—
SolventDimethylformamideHCID 6228—
Product4-(4-Methoxy-phenyl)-1H-indole-2-carboxylic acid (1-benzyl-piperidin-4-yl)-amideHCID 66841881—

Reaction Steps

128 (4.7 g, 17.6 mmol) and 1-benzyl-piperidin-4-ylamine (3.3 g, 17.6 mmol) are dissolved in DMF (70 ml) and after addition of TBTU (6.4 g, 19.4 mmol) and ethyldiisopropylamine (12 ml, 70.4 mmol) the mixture is stirred at room temperature for 2 h. Then the solvent is evaporated at high vacuum. The residue is dissolved in ethyl acetate washed with saturated aqueous sodium hydrogen carbonate and brine. The organic layers are dried over sodium sulfate and evaporated under reduced pressure. The crude mixture is crystallized from methanol.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08183366B2
Source datasetuspto-grants-2012_05
ORD IDord-e261eb93bc0149a6ac20a98520e4c8cf
Source noteuspto-grants-2012_05