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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2074325Generated: October 25, 2026

Dimethylformamide → (Pyridin-3-yl) 4-[(6-phenylhexanoyl)amino]piperidine-1-carboxylate

https://huagongshe.com/reaction/2074325

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant6-Phenylhexanoic AcidHCID 79695—
ReactantSodium BicarbonateHCID 516892—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
SolventWaterHCID 962—
Product(Pyridin-3-yl) 4-[(6-phenylhexanoyl)amino]piperidine-1-carboxylateHCID 57507791—

Reaction Steps

The resulting compound (0.28 g) was dissolved in dimethylformamide (10 ml), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.28 g), 1-hydroxybenzotriazole (0.16 g), TEA (0.54 ml) and 6-phenylhexanoic acid (0.18 g) were added thereto, followed by stirring at room temperature for 15 hours. Water was added to the reaction solution and further stirred for 1 hour. Then, sodium hydrogencarbonate solution was added thereto, followed by extraction with EtOAc. The organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: EtOAc) to obtain a colorless powder. This was recrystallized from methanol and diethyl ether to obtain (pyridin-3-yl) 4-[(6-phenylhexanoyl)amino]piperidine-1-carboxylate (108 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07919495B2
Source datasetuspto-grants-2011_04
ORD IDord-7d255f8065394db7a1c8e8e875eef87e
Source noteuspto-grants-2011_04