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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1928979Generated: October 31, 2026

Potassium Carbonate → {1-[2-(4-Methyl-piperidin-1-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/1928979

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant4-MethylpiperidineHCID 69381—
ReactantDiisopropylethylamineHCID 81531—
Reactant(Cyanomethyl)trimethylphosphanium iodideHCID 10514344—
Reactant[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl esterHCID 45076484—
SolventPropionitrileHCID 7854—
Product{1-[2-(4-Methyl-piperidin-1-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl esterHCID 66841138—

Reaction Steps

A mixture of ester 8 (3 g, 12.28 mmol), 4-methyl piperidine (1.46 ml, 12.28 mmol) and DIEA (2.7 ml, 15.96 mmol) in 30 ml of propionitrile is treated with solid cyanomethyl-trimethyl-phosphonium iodide (3.58 g, 14.74 mmol) and heated at reflux for 3 hours. After cooling to room temperature, a 2M-K2CO3 solution is added until basic and the mixture is extracted twice with DCM. The organic layers are washed with brine, dried over anhydrous sodium sulfate and evaporated. The crude material is purified by chromatography using EtOAc/MeOH (saturated with ammonia): 9/1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08183366B2
Source datasetuspto-grants-2012_05
ORD IDord-65ccf13c7b9c4f4799bf301f2c6279b8
Source noteuspto-grants-2012_05