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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2223713Generated: October 25, 2026

1,1'-Carbonyldiimidazole → 3-[2-(4-Benzyl-piperidin-1-yl)-ethyl]-1-methyl-1-(2-methyl-quinolin-4-yl)-urea

https://huagongshe.com/reaction/2223713

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
ReactantSodium bis(trimethylsilyl)amideHCID 2724254—
Reactant2-(4-Benzylpiperidin-1-yl)ethan-1-amineHCID 2779831—
ReactantN,2-dimethylquinolin-4-amineHCID 13042979—
SolventDimethyl SulfoxideHCID 679—
SolventWaterHCID 962—
Product3-[2-(4-Benzyl-piperidin-1-yl)-ethyl]-1-methyl-1-(2-methyl-quinolin-4-yl)-ureaHCID 17956492—

Reaction Conditions

Temperature20 °C

Reaction Steps

To a stirred solution of CDI (178 mg, 1.1 mmol) in DMSO (5 mL) is added a solution of 2-(4-benzyl-piperidin-1-yl)-ethylamine (218 mg, 1 mmol) in DMSO (1 mL). The reaction mixture is stirred at 20° C. for 3 h. Methyl-(2-methyl-quinolin-4-yl)-amine (173 mg, 1 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 1.25 mL, 2.5 mmol). The reaction mixture is stirred at 20° C. for 24 h, then H2O (0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07375227B2
Source datasetuspto-grants-2008_05
ORD IDord-3925a18c660d4ba7bf8c3fa196ebf96e
Source noteuspto-grants-2008_05