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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1700336Generated: October 26, 2026

Piperidine → 5-(2-Cyanoethyl) 3-benzyl 4-(3-chlorophenyl)-2-dimethoxymethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

https://huagongshe.com/reaction/1700336

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPiperidineHCID 8082—
Reactant3-ChlorobenzaldehydeHCID 11477—
Reactant2-Cyanoethyl 3-aminocrotonateHCID 13671410—
ReactantBenzyl 4,4-dimethoxy-3-oxobutyrateHCID 18318278—
SolventBenzeneHCID 241—
SolventWaterHCID 962—
SolventIsopropanolHCID 3776—
Product5-(2-Cyanoethyl) 3-benzyl 4-(3-chlorophenyl)-2-dimethoxymethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylateHCID 70155198—

Reaction Conditions

Temperature120 °C

Reaction Steps

3.84 g (7.52 mmol) of benzyl 4,4-dimethoxy-3-oxobutyrate, 1.30 ml (11.5 mmol) of 3-chlorobenzaldehyde and 0.114 ml of piperidine were heated under reflux in 11.5 ml of benzene overnight while water was removed. The reaction solution was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue thus obtained and 1.77 g (11.5 mmol) of 2-cyanoethyl 3-aminocrotonate were heated at 70° C. under stirring in 57.5 ml of 2-propanol overnight. The reaction mixture was then heated at 120° C. under stirring under atmospheric pressure for 4 hours while 2-propanol was evaporated. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1) to obtain the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06350762B1
Source datasetuspto-grants-2002_02
ORD IDord-b61d2bee8c8f405ebd5a6f871d7d3521
Source noteuspto-grants-2002_02